(2-Fluoro-4-nitrophenyl)methanol → 2-Fluoro-4-nitrobenzaldehyde

HRID 2252051Notes

Reaction equation

HRID 2252051 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][OH:12]>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH:11]=[O:12]

Participants

3

Reactant 1

HCID 17981733(2-Fluoro-4-nitrophenyl)methanol

Product 1

HCID 45629192-Fluoro-4-nitrobenzaldehydeYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add borane-tetrahydrofuran complex (16.21 mL, 1 M) to a mixture of 2-fluoro-4-nitro-benzoic acid (1.2 g) and tetrahydrofuran (10 mL) at 0° C. Heat at 80° C. for 3 hours. Cool at room temperature and add 1 N aqueous hydrochloric acid (20 mL) and extract with ethyl acetate. Wash with saturated aqueous sodium bicarbonate and dry the remaining organic phase over sodium sulfate and concentrate under reduced pressure to provide (0.91 g, 83%) of an oil. Add (2-fluoro-4-nitro-phenyl)-methanol (0.91 g) to a mixture of dioxide manganese (1.1 g) in 20 ml of dichloromethane. Stir at room temperature overnight and filter over Celite®. Concentrate under reduced pressure to provide (0.27 g, 30%) of the title compound as an oil.

Workup

  1. filtrationfilter over Celite®
  2. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-d2e0fc6311214c75986fb7e07d80d1f3
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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