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

HRID 1582884Notes

Reaction equation

HRID 1582884 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)C=O.ClC1C=CC=C(C(OO)=[O:20])C=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([OH:20])[CH:9]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 906845-Bromo-2-methoxybenzaldehyde

Product 1

HCID 1422285-Bromo-2-methoxyphenolYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-2-methoxybenzaldehyde (2.4 g, 11.2 mmol) in 50 mL CH2Cl2, m-chloroperbenzoic acid (70-75%, 7 g, 28.4 mmol pure m-CPBA,) was added and the mixture was stirred at ambient temperature for 2 days. The reaction was quenched with aqueous saturated NaHCO3 solution and extracted with ethyl acetate (50 mL×3). The organic extract was dried with anhydrous sodium sulfate and filtered through a silica gel bed. Evaporation of the solvent gave compound 35 (2.1 g) in 92% yield; mp 62-64° C.; 1H NMR (CDCl3) δ3.87 (3H, s), 6.71 (1H, d, J=8.6), 6.97 (1H, dd, J1=8.6, J2=2.4), 7.07 (1H, d, J=2.4); 13C NMR δ56.59, 112.36, 113.75, 118.33, 123.29, 146.37, 146.98.

Workup

  1. customThe reaction was quenched with aqueous saturated NaHCO3 solution
  2. extractionextracted with ethyl acetate (50 mL×3)
  3. extractionThe organic extract
  4. dry with materialwas dried with anhydrous sodium sulfate
  5. filtrationfiltered through a silica gel bed
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4183198c71584f44ab08037d49b9b3fc
Source dataset
uspto-grants-2004_05
Patent number
US06740650B2

Reaction notes

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