ChemicalBook CAS DataBase List 4-FLUORO-2-HYDROXYBENZALDEHYDE

4-FLUORO-2-HYDROXYBENZALDEHYDE synthesis

5synthesis methods

Product Name:4-FLUORO-2-HYDROXYBENZALDEHYDE
CAS Number:348-28-7
Molecular formula:C7H5FO2
Molecular Weight:140.11

50-00-0 Synthesis

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372-20-3 Synthesis

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348-28-7
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Yield:348-28-7 72%

Reaction Conditions:

with triethylamine;magnesium chloride in acetonitrile for 5 h;Heating / reflux;

Steps:

612.a.1 Example 612a; 7- (ISOBUTYLAMINO)-2- (TRIFLUOROMETHYL)-2H-CHROMENE-3-CARBOXYLIC acid; Step 1. Preparation of 2-HVDROXY-4-FLUOROBENZALDEHYDE.
[1042] To the mixture of 3-fluorophenol (10 mL, 102 mmole), anhydrous magnesium chloride (28.2 g, 744.6 mmole) in 500 mL of anhydrous acetonitrile was added anhydrous triethylamine (67 mL, 382. 5 mmole) and paraformaldehyde (22.3 g, 744.6 mmole). The mixture was then heated to reflux for five hours. After cooling to r. t, 500 mL of 5% aqueous hydrochloric acid was added. The product was extracted with ethyl acetate. The combined organic extracts were washed with 5% hydrochloric acid (x 3), brine, and dried over anhydrous magnesium sulfate. After removing the volatiles, the residue was a light pink solid. 11 g, yield 72%. M. P: 67.5-69. 0°C. ESHRMS 777/Z 139.0211 (M-H, C7H4FO2 calc'd 139. 0201). 1H NMR (CDCl3/300MHz) 11.40 (s, 1H), 9.86 (s, 1H), 7.62-7. 57 (m, 1H), 6.79-6. 67 (m, 2H). 13C (CDC13/300MH) 195.4, 168.3 (d, J= 258 HZ), 164.4 (d, J=14. 9 Hz), 136.3 (d, J=12. 6 Hz), 118.2 (d, J= 2.0Hz), 108.5 (d, J= 23. 3 Hz), 104.9 (d, J=24. 4 HZ). L9F (CDCl3/400MHz) -97. 9 (m).

References:

PHARMACIA CORPORATION WO2004/87686, 2004, A2 Location in patent:Page 504 PHARMACIA CORPORATION WO2004/87687, 2004, A1 Location in patent:Page 504

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50-00-0 Synthesis

50-00-0
865 suppliers
$10.00/25g

372-20-3 Synthesis

372-20-3
375 suppliers
$7.00/5g