5-Methylbenzofuran → 5-(Bromomethyl)benzofuran

HRID 1004958Notes

Reaction equation

HRID 1004958 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]2[O:6][CH:7]=[CH:8][C:4]=2[CH:3]=1.[Br:11]N1C(=O)CCC1=O.BrCC1C=CC2SC=CC=2C=1.CC1C=CC2SC=CC=2C=1>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[CH:10]=[CH:9][C:5]2[O:6][CH:7]=[CH:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 331035-MethylbenzofuranHCID 67184N-bromobutanimideHCID 843465-Methylbenzo(b)thiopheneHCID 111604985-(Bromomethyl)benzo[b]thiophene

Product 1

HCID 221285225-(Bromomethyl)benzofuran

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

By brominating 5-methyl-benzo[b]furan[Synth. Commun. 19, 257(1989)] with N-bromosuccinimide in carbon tetrachloride in an analogous manner to the procedure for the preparation of 5-bromomethyl-benzo[b]thiophene [J. Med. Chem. 34(1), 65(1991)] from 5-methyl-benzo[b]thiophene there was obtained 5-bromomethyl-benzo[b]furan as a light yellow solid; MS: 210, 212 (M)+.

Sources & evidence

ORD record
ord-21137035b803423d9f2fc489f1a767c3
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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