m-Chloroperbenzoic acid → 5-Bromo-2-methoxyphenol

To a solution of 5-bromo-2-methoxy-benzaldehyde (8 g, 4.67 mmol) dissolved in methylene chloride (24 mL) at 0° C. is slowly added a solution of m-chloroperoxybenzoic acid (10.90 g, 5.60 mmol) in methylene chloride (80 mL). The reaction mixture is slowly warmed up to room temperature and stirred for 72 h. The white solid is filtered off and the filtrate is stirred for 2 h with 2 M sodium sulfite (32 mL). The organic layer is concentrated in vacuo then the residue is dissolved in diethyl ether and washed with 1 M sodium sulfite and a half-saturated sodium bicarbonate solution. The organic phase is extracted with 2 M sodium hydroxide. The combined basic extract is acidified to pH 3-4 with concentrated HCl, and extracted with diethyl ether. The combined organic extracts are washed with a saturated sodium chloride solution, dried with magnesium sulfate, and concentrated in vacuo to provide 3.5 g (37%) of the title compound as a brown solid. 1H NMR (CDCl3): δ 7.10 (d, J=2 Hz, 1H), 7.00 (dd, J=8, 2 Hz, 1H), 6.70 (d, J=8 Hz, 1H), 3.95 (s, 3H).

1. filtrationThe white solid is filtered off
2. stirringthe filtrate is stirred for 2 h with 2 M sodium sulfite (32 mL)
3. concentrationThe organic layer is concentrated in vacuo
4. dissolutionthe residue is dissolved in diethyl ether
5. washwashed with 1 M sodium sulfite
6. extractionThe organic phase is extracted with 2 M sodium hydroxide
7. extractionThe combined basic extract
8. extractionextracted with diethyl ether
9. washThe combined organic extracts are washed with a saturated sodium chloride solution
10. dry with materialdried with magnesium sulfate
11. concentrationconcentrated in vacuo

ORD record

ord-28567837d7164e15b9d8bc19feb2d0a6

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08975439B2