Carbon tetrabromide → 3-(2-Bromoethyl)-5-fluorobenzofuran

HRID 1358242Notes

Reaction equation

HRID 1358242 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([CH2:10][CH2:11]O)[C:6]=2[CH:13]=1.[Br:14]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[Br:14][CH2:11][CH2:10][C:7]1[C:6]2[CH:13]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:9][CH:8]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18184294HCID 18184294, compound

Product 1

HCID 181842963-(2-Bromoethyl)-5-fluorobenzofuranYield 105.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-(5-fluorobenzofuran-3-yl)ethanol (5.2 g) and tetrabromomethane (11.6 g) in acetonitrile (175 mL) was treated with triphenylphosphine (8.3 g) at 0° C. After stirring for 15 min, the mixture was concentrated in vacuo an the resulting oil was applied to a silica gel flash column (eluent: heptane/ethyl acetate 65:35) resulting in an oil, 3-(2-bromoethyl)-5-fluorobenzofuran (7.4 g).

Workup

  1. concentrationthe mixture was concentrated in vacuo an the resulting oil

Sources & evidence

ORD record
ord-7583c66373cf4db1b81f2cf267946e17
Source dataset
uspto-grants-2003_07
Patent number
US06596722B2

Reaction notes

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