Carbon tetrabromide → 2-(Bromomethyl)-1-benzofuran

HRID 594315Notes

Reaction equation

HRID 594315 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10]O.C(Br)(Br)(Br)[Br:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:13][CH2:10][C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 27762631-Benzofuran-2-Ylmethanol

Product 1

HCID 123263162-(Bromomethyl)-1-benzofuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzofuran-2-ylmethanol (120 mg; 0.81 mmol) in anh. DCM (5 ml) was treated at rt with CBr4 (268 mg; 0.81 mmol), and with PPh3 (212 mg; 0.81 mmol). The resulting mixture was further stirred at rt, under nitrogen, for 17 h. Concentration to dryness under reduced pressure, and subsequent purification by FC (DCM) afforded 2-(bromomethyl)benzofuran as a yellow oil (128 mg; 75%) which was directly used for the next reaction.

Workup

  1. concentrationConcentration to dryness
  2. customunder reduced pressure, and subsequent purification by FC (DCM)

Sources & evidence

ORD record
ord-d9a89dc8e5b345cd95202de71e5886a7
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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