(3-Bromo-5-fluorophenyl)methanol → 3-Bromo-5-fluorobenzaldehyde

HRID 912042Notes

Reaction equation

HRID 912042 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[CH:9]=[O:10]

Participants

4

Reactant 2

HCID 2769402(3-Bromo-5-fluorophenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 219862463-Bromo-5-fluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3-Bromo-5-fluorophenyl)methanol (378 mg, 1.86 mmol) was dissolved in DCM (10 ml), into which was added pyridinium chlorochromate (880 mg, 4.00 mmol). The mixture was stirred at rt under an atmosphere of nitrogen for 16 h. After that time, the reaction mixture was passed through a silica gel plug, eluting with DCM (250 ml) to give the title compound as a brown solid. 1H NMR (400 MHz, CDCl3): δ=7.50-7.54 (m, 2H), 7.81-7.83 (m, 1H), 9.33 (d, J=2.0 Hz, 1H). HPLC: tR=3.27 min (polar—5 min, ZQ3).

Workup

  1. washeluting with DCM (250 ml)

Sources & evidence

ORD record
ord-558a66c59c70477f9a9663d26426b221
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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