Phosphorus tribromide → 1-(1-Bromoethyl)-3-chlorobenzene

HRID 1749148Notes

Reaction equation

HRID 1749148 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8](O)[CH3:9])[CH:5]=[CH:6][CH:7]=1.[Br:11]P(Br)Br>C(OCC)C>[Br:11][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH3:9]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 977793-Chloro-alpha-methylbenzenemethanol

Product 1

HCID 99208551-(1-Bromoethyl)-3-chlorobenzeneYield 57.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 1-(3-chlorophenyl)ethanol (0.2 g, 1.28 mmol) in diethyl ether (10 mL) at 0° C. was added tribromophosphine (0.38 g, 1.41 mmol). The mixture was warmed to room temperature and stirred overnight, then diluted with ether (10 mL). After quenching with water (10 mL), the organic phase was separated, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel and eluted with petroleum ether to give the title compound as an oil (0.16 g, yield 57.1%).

Workup

  1. customAfter quenching with water (10 mL)
  2. customthe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluted with petroleum ether

Sources & evidence

ORD record
ord-df6d0d12edc2492ab712112b67369dda
Source dataset
uspto-grants-2015_10
Patent number
US09156788B2

Reaction notes

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