Benzoyl Peroxide → Ethyl 3-Bromomethyl-5-chlorobenzo[b]thiophene-2-carboxylate

HRID 343277Notes

Reaction equation

HRID 343277 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[S:6][C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:8]([CH3:9])[C:4]=2[CH:3]=1.[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:9][C:8]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:16]=[CH:15][C:5]=2[S:6][C:7]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 14836260Ethyl 5-chloro-3-methyl-1-benzothiophene-2-carboxylate

Product 1

HCID 14836261Ethyl 3-Bromomethyl-5-chlorobenzo[b]thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of ethyl 5-chloro-3-methylbenzo(b)thiophene-2-carboxylate (9.0 g, 0.035 mol), N-bromosuccinimide (6.53 g, 0.037 mol) and benzoyl peroxide (130 mg) in carbon tetrachloride (150 ml) was refluxed and illuminated with sunlamp for 2 hours. The resulting suspension was cooled, filtered and the filter cake was triturated with methanol to give 9.9 g, (85%) of the methanol-insoluble ethyl 3-bromomethyl-5-chlorobenzo(b)thiophene-2-carboxylate: mp 148°-150° C.

Workup

  1. temperaturewas refluxed
  2. customilluminated with sunlamp for 2 hours
  3. temperatureThe resulting suspension was cooled
  4. filtrationfiltered
  5. customthe filter cake was triturated with methanol
  6. customto give 9.9 g, (85%) of the methanol-insoluble ethyl 3-bromomethyl-5-chlorobenzo(b)thiophene-2-carboxylate

Sources & evidence

ORD record
ord-63b1db53595e48458e37f1fae887e54d
Source dataset
uspto-grants-1999_01
Patent number
US05861309

Reaction notes

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