(4-Bromo-3-chlorophenyl)methanol → 4-Bromo-3-chlorobenzaldehyde

HRID 1501127Notes

Reaction equation

HRID 1501127 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[Cl:10].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[Cl:10]

Participants

4

Reactant 2

HCID 53255486(4-Bromo-3-chlorophenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 140498064-Bromo-3-chlorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of (4-bromo-3-chlorophenyl)methanol (2.0 g, 9.0 mmol), pyridinium chlorochromate (2912 mg, 13.5 mmol) in dichloromethane (50 mL0 was stirred at 25° C. for 3 hours. The mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ethe/ethyl acetate=1:1) to give 4-bromo-3-chlorobenzaldehyde as a white solid (1.6 g g, 81%). 1H NMR (300 MHz, d6-DMSO): δ 9.96 (s, 1H), 7.69 (d, J=8.1, 1H), δ 7.53 (d, J=0.9, 1H), 7.19 (dd, J=8.1, 1H J2=0.9, 1H)

Workup

  1. concentrationThe mixture was concentrated
  2. customto give a residue
  3. customThe residue was purified by column chromatography (silica gel, petroleum ethe/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ef10a1a3c9b24cdca3b790bca30d5134
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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