Benzoyl Peroxide → Methyl 4-(bromomethyl)-3-chlorothiophene-2-carboxylate

HRID 370078Notes

Reaction equation

HRID 370078 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[C:8]([CH3:11])[C:9]=1[Cl:10])=[O:4].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[C:8]([CH2:11][Br:12])[C:9]=1[Cl:10])=[O:4]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2777567Methyl 3-chloro-4-methylthiophene-2-carboxylate

Product 1

HCID 18376575Methyl 4-(bromomethyl)-3-chlorothiophene-2-carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 2-methoxycarbonyl-3-chloro-4-methylthiophene (0.25 g, 1.3 mmol) in dry benzene (25 mL) were added N-bromosuccinimide (0.28 g, 1.6 mmol) and benzoyl peroxide (0.03 g, 0.13 mmol). The mixture was refluxed while irradiating with a 250 Watt lamp. After 2 hours the reaction was cooled and concentrated of all volatiles in vacuo. Purification by flash chromatography on silica gel afforded 0.20 g (58% yield) of 2-methoxycarbonyl-3-chloro-4-(bromomethyl)thiophene as a white solid; NMR (CDCl3) 7.6 (s, 1), 4.4 (s, 2), 3.9 (s, 3) ppm.

Workup

  1. temperatureThe mixture was refluxed
  2. customwhile irradiating with a 250 Watt lamp
  3. temperatureAfter 2 hours the reaction was cooled
  4. concentrationconcentrated of all volatiles in vacuo
  5. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-4e0d56fe4f864d9092e91eb1a2823e42
Source dataset
uspto-grants-2000_10
Patent number
US06140351

Reaction notes

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