Benzoyl chloride → 2-Benzoyl-5-methoxybenzoic acid

Temperature

-78 °C

A solution of 2-bromo-5-methoxybenzoic acid (5 g, 21.6 mmol) in 50 mL of THF is stirred under argon at −78° C., and a 1.6 M solution of n-butyllithium in hexane (29 mL, 45 mmol) is then added dropwise. The reaction mixture is stirred for 1 hour at −78° C. and benzoyl chloride (3.2 g, 22.7 mmol) is then added dropwise. The reaction mixture is stirred for 1 hour 30 minutes at −78° C. and then for 18 hours at room temperature. The mixture is hydrolysed with 100 mL water and then washed with ethyl acetate. The aqueous phase is acidified by addition of 5 N hydrochloric acid and then extracted with ethyl acetate. The organic phase obtained is washed with brine and then dried over anhydrous sodium sulfate. After filtration and evaporation under reduced pressure, 5.4 g of a colourless oil are obtained, and are used without purification.

1. stirringThe reaction mixture is stirred for 1 hour 30 minutes at −78° C.
2. waitfor 18 hours at room temperature
3. washwashed with ethyl acetate
4. additionThe aqueous phase is acidified by addition of 5 N hydrochloric acid
5. extractionextracted with ethyl acetate
6. customThe organic phase obtained
7. washis washed with brine
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationAfter filtration and evaporation under reduced pressure, 5.4 g of a colourless oil
10. customare obtained
11. customare used without purification

ORD record

ord-925758cac70f47c8b4ab12e182b17ff3

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07423030B2