Water → 1-Bromo-3-(bromomethyl)-4-chloro-2-fluorobenzene
Reaction equation
P(Br)(Br)[Br:2].[Br:5][C:6]1[C:7]([F:15])=[C:8]([CH2:13]O)[C:9]([Cl:12])=[CH:10][CH:11]=1.O>ClCCl>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([CH2:13][Br:2])[C:7]=1[F:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Add phosphorous tribromide (1.8 mL, 19.2 mmol) to (3-bromo-6-chloro-2-fluoro-phenyl)methanol (Preparation 8) (4.6 g, 19 mmol) in dichloromethane (50 mL) at 0° C. Stir for 20 minutes. Add the reaction mixture into ice and water. Extract with dichloromethane (100 mL), dry with magnesium sulfate, filter and evaporate solvent under reduced pressure. Purify the residue by biotage chromatography to yield the product to give 1.7 g (30%) of the title compound as a white solid. 1HNMR (CDCl3) 7.48-7.44 (m, 1H), 7.14-7.11 (m, 1H), 4.62-4.61(m, 2H).
Workup
- extractionExtract with dichloromethane (100 mL)
- dry with materialdry with magnesium sulfate
- filtrationfilter
- customevaporate solvent under reduced pressure
- customPurify the residue by biotage chromatography
- customto yield the product
Sources & evidence
- ORD record
- ord-ba88538709ef4fb6b226b3518c7d47d3
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07713979B2
Reaction notes
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