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

HRID 1465949노트

반응식

HRID 1465949 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 241Benzene용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3dfb7a3993ad439aa230bbbfca37c8b3
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000006B2

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