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

HRID 1465949ノート

反応式

HRID 1465949 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[C:8]([Br:11])[C:9]=1[CH3:10])=[O:4].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[C:8]([Br:11])[C:9]=1[CH2:10][Br:12])=[O:4]

参加物

6

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 59212115Methyl 4-bromo-3-methylthiophene-2-carboxylate

生成物 1

HCID 67233904Methyl 4-bromo-3-(bromomethyl)thiophene-2-carboxylate収率 56.7%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

4-Bromo-3-methyl-thiophene-2-carboxylic acid methyl ester (3.0 g, 12.8 mmol), example 31-a, N-bromosuccinimide (2.33 g, 13.1 mmol), and benzoyl peroxide (310 mg, 1.28 mmol) were suspended in 32 mL of benzene and heated at reflux temperature for 16 hours. The reaction mixture was cooled and diluted with ethyl acetate. The reaction mixture was washed successively with saturated bicarbonate solution, brine, saturated ammonium chloride solution, and brine. The organic solvent was dried, filtered, and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-40% ethyl acetate in hexanes to produce 2.28 g of a yellow solid. NMR (CDCl3, 200 MHz): δ=7.48 (s, 1H), 4.91 (s, 2H), and 3.94 (s, 3H).

後処理

  1. temperatureheated
  2. temperatureat reflux temperature for 16 hours
  3. temperatureThe reaction mixture was cooled
  4. washThe reaction mixture was washed successively with saturated bicarbonate solution, brine, saturated ammonium chloride solution, and brine
  5. customThe organic solvent was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography
  9. washeluting from silica gel with a gradient of 0-40% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-3dfb7a3993ad439aa230bbbfca37c8b3
出典データセット
uspto-grants-2015_04
特許番号
US09000006B2

反応ノート

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