Benzylmagnesium chloride synthesis
- Product Name:Benzylmagnesium chloride
- CAS Number:6921-34-2
- Molecular formula:C7H7ClMg
- Molecular Weight:150.89
100-44-7
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103-29-7
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$9.00/25g
6921-34-2
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$53.20/100ml
Yield:6921-34-2 83%
Reaction Conditions:
with magnesium in tetrahydrofuran;2-methyltetrahydrofuran at 60; under 5171.62 Torr;Inert atmosphere;Flow reactor;Solvent;Temperature;
Steps:
1.2.3. Grignard reagents (RMgX)
General procedure: Bromoethane (3.336 g, 2.28 mL, 30.00 mmol, 1 equiv) is dissolved in THF (22.7 mL) in a flask under argon. The organohalide 1.2 M solution is flowed through activated magnesium (chips/powder 1:1 wt %, 1.49 g, 60 mmol, 2 equiv) with BPR (100 psi) at 0.5 mL/min and 25 °C (Figure S1). After ≈4 min, the outcome solution is collected in a vial containing 2-hydroxybenzaldehyde phenylhydrazone (20-40 mg). When the yellow color solution turns orange, Grignard reagent solution is collected in a flask under argon. When the starting material solution is consumed, organomagnesium collection is maintained during 4 min (≈2-fold the residence time), pumping THF at 0.5 mL/min, yielding 90% of ethylmagnesium bromide as clear 1.08 M solution (≈20 mL, the yield is calculated in a steady state because the discarded volume of head and tail solution is constant, independently of the volume of organohalide solution converted). The concentration determination with 2-hydroxybenzaldehyde phenylhydrazone (82.3 mg, 0.38 mmol) dissolved in THF (1 mL) consumed 0.37 mL of EtMgBr corresponding to 1.03 M. The concentration determination with benzoic acid (46.2 mg, 0.37 mmol) and 4-(phenylazo)diphenylamine (indicator) dissolved in THF (1 mL) consumed 0.33 mL of EtMgBr corresponding to 1.12 M.
References:
Adamo, Andrea;Berton, Mateo;McQuade, D. Tyler;Sheehan, Kevin [Beilstein Journal of Organic Chemistry,2020,vol. 16,p. 1343 - 1356] Location in patent:supporting information
100-44-7
644 suppliers
$13.50/250G
6921-34-2
229 suppliers
$53.20/100ml
100-39-0
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$10.00/10 g
6921-34-2
229 suppliers
$53.20/100ml
100-44-7
644 suppliers
$13.50/250G
613-12-7
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$203.00/1g
103-29-7
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$9.00/25g
108-88-3
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$21.80/5 mL
6921-34-2
229 suppliers
$53.20/100ml
100-44-7
644 suppliers
$13.50/250G
6921-34-2
229 suppliers
$53.20/100ml