4-Fluoro-3-hydroxybenzoic acid → 3-Ethoxy-4-fluorobenzaldehyde

HRID 547920Notes

Reaction equation

HRID 547920 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH2:11][CH3:12].[F:13]C1C=CC(C(O)=O)=CC=1O>>[CH2:11]([O:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[F:13])[CH:6]=[O:7])[CH3:12]

Participants

3

Reactant 2

HCID 5936354-Fluoro-3-hydroxybenzoic acidHCID 547756424-Chloro-3-ethoxybenzaldehyde2×

Product 1

HCID 426142943-Ethoxy-4-fluorobenzaldehyde

Procedure

The title compound was prepared according to the procedure described for the synthesis of 4-chloro-3-ethoxy-benzaldehyde (intermediate B2, vide infra) starting from 4-fluoro-3-hydroxy-benzoic acid in 73% overall yield after purification by flash column chromatography on silica eluting with hexane/ethyl acetate (10:1). 1H NMR (300 MHz, DMSO): δ 1.32 (t, J=7.0 Hz, 3H), 4.12 (q, 7.0 Hz, 2H), 7.34-7.41 (m, 1H), 7.47-7.56 (m, 2H), 9.87 (s, 1H). MS (ISP): 186.1 [M+NH4]+.

Workup

  1. customoverall yield
  2. customafter purification by flash column chromatography on silica eluting with hexane/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-a76fcec97b3540508746d04dc401a4fc
Source dataset
uspto-grants-2011_05
Patent number
US07939661B2

Reaction notes

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