Carbon tetrabromide → HCID 57494373, compound

HRID 558071Notes

Reaction equation

HRID 558071 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH2:12][CH2:13]O)[CH:9]=[CH:10][CH:11]=1.C(Br)(Br)(Br)[Br:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[CH2:12][CH2:13][Br:16]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57429962HCID 57429962, compound

Product 1

HCID 57494373HCID 57494373, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(3-furan-2-yl-phenyl)ethanol and carbon tetrabromide in DCM was treated with triphenylphosphine at 0° C. The resultant mixture was stirred at room temperature for one hr. The volatiles were removed under reduced pressure. Purification by column chromatography (5% ethyl acetate/hexanes) gave 3-(2-furyl)phenethyl bromide. 1H NMR (CDCl3) δ 7.57 (d, J=1.6, 1H), 7.55 (s, 1H), 7.47 (s, 1H), 7.33 (t, J=8.0 Hz, 1H), 7.11 (d, J=8.0 Hz, 1H), 6.66 (m, 1H), 6.47 (m, 1H), 3.60 (t, J=7.2 Hz, 2H), 3.20 (t, J=7.2 Hz, 2H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customPurification by column chromatography (5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8adcb260779e45e3b39a87e478082fa2
Source dataset
uspto-grants-2011_11
Patent number
US08063021B2

Reaction notes

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