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

5-Bromo-2-methoxy-phenol was synthesized by dissolving 5-bromo-2-methoxy-benzaldehyde (50 g, 233 mmol), in CH2Cl2 (150 mL) was cooled with an ice bath to 0° C., and subsequently, 3-chloroperoxybenzoic acid (70-75% purity) (68.1 g, 276 mmol) in CH2Cl2 (500 mL) was added. The reaction mixture was allowed to warm slowly to room temperature and stirred for 72 h. The colorless solid was filtered off, and the filtrate was stirred for 2 h with a 2 N Na2SO3 solution (200 mL). The organic layer was evaporated and the remainder dissolved in diethyl ether and washed with 1 N Na2SO3 and a half saturated NaHCO3 solution. The organic phase was extracted with a 2 N aqueous NaOH solution. The combined basic extract was acidified (pH ˜3-4) with concentrated HCl and then extracted with diethyl ether. The combined organic extracts were dried over MgSO4, filtered, and the solvent evaporated to afford intermediate 5-bromo-2-methoxy-phenol (43.5 g, 90%). 1H NMR (CDCl3) 7.06 (d, J=2.3, 1H), 6.96 (dd, J=8.6, 2.3, 1H), 6.70 (d, J=8.6, 1H), 5.67 (s, 1H), 3.86 (s, 3H).

1. custom5-Bromo-2-methoxy-phenol was synthesized
2. filtrationThe colorless solid was filtered off
3. stirringthe filtrate was stirred for 2 h with a 2 N Na2SO3 solution (200 mL)
4. customThe organic layer was evaporated
5. dissolutionthe remainder dissolved in diethyl ether
6. washwashed with 1 N Na2SO3
7. extractionThe organic phase was extracted with a 2 N aqueous NaOH solution
8. extractionThe combined basic extract
9. extractionextracted with diethyl ether
10. dry with materialThe combined organic extracts were dried over MgSO4
11. filtrationfiltered
12. customthe solvent evaporated

ORD record

ord-1e0aad31ec144033b2699a618b1725fa

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927546B2