ChemicalBook CAS DataBase List 3-Bromotoluene

3-Bromotoluene synthesis

10synthesis methods

Product Name:3-Bromotoluene
CAS Number:591-17-3
Molecular formula:C7H7Br
Molecular Weight:171.03

Synthesis of 3-Bromotoluene: It is derived from 3-bromo-4-aminotoluene by diazotization and reduction. The mixture of 95% ethanol, concentrated sulfuric acid and 3-bromo-4-aminotoluene was stirred and cooled to 10°C, and sodium nitrite solution was added to keep the reaction temperature not exceeding 10°C. After adding, continue stirring for 20min. Add the copper powder washed with ether, heat carefully, stop heating after the reaction starts, nitrogen will be released violently, and acetaldehyde will be formed. Then steam distillation is carried out until no oily substance evaporates. Separate the organic phase from the distillate and wash with 10% sodium hydroxide, water, concentrated sulfuric acid, and 5% sodium carbonate solution in sequence. Dry with anhydrous calcium chloride, filter, distill, collect 180-183 ℃ (99.75kPa) fractions to obtain colorless pure 3-bromotoluene with a yield of over 50%.

625-95-6
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591-17-3
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$10.00/10g

Yield:591-17-3 72%

Reaction Conditions:

with bis(1,5-cyclooctadiene)nickel ⁽⁰⁾;tetrabutylammonium bromide;4,4′-di-tert-butyl-2,2′-bipyridine in 1,4-dioxane at 20; for 36 h;Schlenk technique;Glovebox;Irradiation;Sealed tube;

Steps:

14 Preparation of 1f(X1=Br, R1=3-Me)

In the glove box, weigh the dry catalyst Ni(COD)2 (5.5mg, 0.02mmol, 10mol%) and dtbbpy (6.4mg, 0.024mmol, 12mol%) into a 10ml dry and clean schlenk tube equipped with a stirring bar, add 1,4-dioxane (1 ml), stirred at room temperature for 10 minutes. Weigh tetrabutylammonium bromide (128.8mg, 0.4 mmol), corresponding 2f (X2=I, R1=3-Me) (23.6mg, 0.2mmol), then add 1ml CPME, seal and irradiate with blue light at 455nm The reaction was carried out at room temperature for 36 hours, and the yield was 72%. 1f

References:

CN115010563,2022,A Location in patent:Paragraph 0063-0065