Bromosuccinimide → Ethyl 3-bromomethyl-5-chloro-2-benzofurancarboxylate

HRID 1111101Notes

Reaction equation

HRID 1111101 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:7]([CH3:15])[C:6]=2[CH:16]=1.[Br:17]C1CC(=O)NC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:17][CH2:15][C:7]1[C:6]2[CH:16]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:9][C:8]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 38309BromosuccinimideHCID 15643819Ethyl 5-chloro-3-methylbenzofuran-2-carboxylate

Product 1

HCID 15678689Ethyl 3-bromomethyl-5-chloro-2-benzofurancarboxylateYield 76%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of ethyl 5-chloro-3-methyl-2-benzofurancarboxylate (52.5 g, 0.22 mol), N bromosuccinimide (39.15 g, 0.22 mol) and benzoyl peroxide (0.4 g) in carbon tetrachloride (750 ml) was stirred and refluxed for 10 hours. The mixture was cooled, filtered and the filtrate was concentrated. The crude product was recrystallized from hexane to give 52.8 g (76%) of ethyl 3-bromomethyl-5-chloro-2-benzofurancarboxylate: mp 112°-114° C.

Workup

  1. temperaturerefluxed for 10 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe crude product was recrystallized from hexane

Sources & evidence

ORD record
ord-95ba2ae6c9f7495f9ff9abc4df0ff517
Source dataset
uspto-grants-1990_12
Patent number
US04978660

Reaction notes

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