Carbon tetrabromide → 2-(Bromomethyl)benzo[b]thiophene

HRID 594313Notes

Reaction equation

HRID 594313 reaction equation
[S:1]1[C:5]([CH2:6]O)=[CH:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.C(Br)(Br)(Br)[Br:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:13][CH2:6][C:5]1[S:1][C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 27763352-(Hydroxymethyl)benzo[b]thiophene

Product 1

HCID 136426052-(Bromomethyl)benzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of commercially available benzo[b]thiophen-2-ylmethanol (123 mg; 0.73 mmol) in anh. DCM (5 ml) was treated at rt with CBr4 (242 mg; 0.73 mmol), and with PPh3 (191 mg; 0.73 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)benzo[b]thiophene as a yellow/orange oil 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-4abaf3b9cde742ecb99f4b4e7deaf1a3
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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