(4-Bromo-3-chlorophenyl)methanol → (4-Bromo-2-chlorophenyl)methanol
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1Cl.[Cr]([Cl:15])([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([Cl:15])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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-2-chlorophenyl)methanol as a white solid (4.12 g g, 81%). 1H NMR (300 MHz, d6-DMSO): δ 9.96 (s, 1H), 7.69 (d, J=8.1, 1H), 7.53 (d, J=0.9, 1H), 7.19 (dd, J1=8.1, 1H J2=0.9, 1H).
Workup
- concentrationThe mixture was concentrated
- customto give a residue
- customThe residue was purified by column chromatography (silica gel, petroleum ethe/ethyl acetate=1:1)
Sources & evidence
- ORD record
- ord-7694f11d22ad4a47a04bd8f2989836f1
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206128B2
Reaction notes
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