Phosphorus tribromide → 4-Bromo-1-(1-bromoethyl)-2-fluorobenzene

HRID 1525864Notes

Reaction equation

HRID 1525864 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH3:9])=[C:4]([F:11])[CH:3]=1.P(Br)(Br)[Br:13]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([Br:13])[CH3:9])=[C:4]([F:11])[CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 596944341-(4-Bromo-2-fluorophenyl)ethanol

Product 1

HCID 829694964-Bromo-1-(1-bromoethyl)-2-fluorobenzeneYield 145.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(4-bromo-2-fluorophenyl)ethanol (8.95 mmol) in dichloromethane (40 mL) at 0° C. was treated dropwise with a solution of phosphorus tribromide (3.58 mmol) in dichloromethane (10 mL). The reaction mixture was allowed to warm to room temperature and was stirred overnight. The solution was concentrated to a residue in vacuo. Purification of the residue by silica gel chromatography (hexanes) yielded the title compound as a clear oil (1.47 g, 58.3% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.00 (d, J=6.82 Hz, 3 H) 5.58 (q, J=7.07 Hz, 1 H) 7.47 (dd, J=8.34, 1.77 Hz, 1 H) 7.57-7.65 (m, 2 H).

Workup

  1. concentrationThe solution was concentrated to a residue in vacuo
  2. customPurification of the residue by silica gel chromatography (hexanes)

Sources & evidence

ORD record
ord-0899ff0eaee746ccb67adef87e6e7196
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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