Water → 1-Bromo-3-(bromomethyl)-4-chloro-2-fluorobenzene

HRID 2235186Notes

Reaction equation

HRID 2235186 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

HCID 962WaterHCID 24614Phosphorus tribromideHCID 59299314(3-Bromo-6-chloro-2-fluorophenyl)methanol

Product 1

HCID 592994321-Bromo-3-(bromomethyl)-4-chloro-2-fluorobenzeneYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. extractionExtract with dichloromethane (100 mL)
  2. dry with materialdry with magnesium sulfate
  3. filtrationfilter
  4. customevaporate solvent under reduced pressure
  5. customPurify the residue by biotage chromatography
  6. 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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