N-bromobutanimide → Ethyl 3-bromomethyl-5-chloro-2-benzofurancarboxylate

HRID 703059Notes

Reaction equation

HRID 703059 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]N1C(=O)CCC1=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 67184N-bromobutanimideHCID 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-d6ed634cb98242d48a6e4f97d0258e84
Source dataset
uspto-grants-1991_01
Patent number
US04981849

Reaction notes

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