Carbon tetrabromide → 1-(2-Bromoethyl)-3-fluorobenzene

HRID 1419773Notes

Reaction equation

HRID 1419773 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6]O.C(Br)(Br)(Br)[Br:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6][Br:12]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 5731322-(3-Fluorophenyl)ethanol

Product 1

HCID 5731291-(2-Bromoethyl)-3-fluorobenzeneYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(fluoro)phenethyl alcohol (3.8 g, 27.0 mmol), in anhydrous dichloromethane (100 ml), cooled to 0° C., was added carbon tetrabromide (11.25 g, 34.0 mmol) and triphenylphosphine (10.62 g, 41.0 mmol). After stirring for 0.5 h the solvent was removed in vacuo and diethyl ether (100 ml) was added to the residue. The resultant precipitate was removed by filtration, the filtrate evaporated under reduced pressure and the crude product chromatographed on silica-gel eluting with ethyl acetate/hexane (1:1) to give 3-(fluoro)phenethyl bromide (5.51 g, 100%), δ (250 MHz, CDCl3) 3.16 (2H, t, J=7.4 Hz, CH2), 3.57 (2H, t, J=7.4 Hz, CH2), 6.91-7.01 (3H, m, Ar--H), 7.24-7.33 (1H, m, Ar--H).

Workup

  1. customwas removed in vacuo and diethyl ether (100 ml)
  2. additionwas added to the residue
  3. customThe resultant precipitate was removed by filtration
  4. customthe filtrate evaporated under reduced pressure
  5. customthe crude product chromatographed on silica-gel
  6. washeluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-c8d7537a40c045f398fe54e620df6991
Source dataset
uspto-grants-1999_03
Patent number
US05889008

Reaction notes

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