p-Toluenesulfonic acid → Ethyl 1-(3-bromophenyl)cyclopropanecarboxylate

HRID 931089

反応式

HRID 931089 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:11]([OH:13])=[O:12])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[C:14]1(C)C=CC(S(O)(=O)=O)=C[CH:15]=1>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 167697291-(3-Bromophenyl)cyclopropane-1-carboxylic acid

生成物 1

HCID 66765078Ethyl 1-(3-bromophenyl)cyclopropanecarboxylate収率 435.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

1-(3-Bromophenyl)cyclopropanecarboxylic acid (976 mg, 4.05 mmol) was dissolved in ethanol (20 mL) and p-toluenesulfonic acid (139 mg, 0.810 mmol) was added. The reaction mixture was heated at reflux for 15 h. The temperature of the oil bath was increased from 80° C. to 110° C. and the reaction mixture was stirred for 2 h at that temperature, after which the mixture was cooled and the solvent was removed under reduced pressure. The crude material was purified via flash chromatography (pentane:ethyl acetate 9:1) to afford ethyl 1-(3-bromophenyl)cyclopropanecarboxylate as a colorless oil (950 mg, 87.2%). 1H NMR (400 MHz, CDCl3) δ 1.13-1.20 (m, 5H), 1.57-1.62 (m, 2H), 4.10 (q, 2H), 7.17 (s, 1H), 7.27 (s, 1H), 7.38 (s, 1H), 7.47-7.50 (m, 1H).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 15 h
  3. temperatureThe temperature of the oil bath was increased from 80° C. to 110° C.
  4. temperatureafter which the mixture was cooled
  5. customthe solvent was removed under reduced pressure
  6. customThe crude material was purified via flash chromatography (pentane:ethyl acetate 9:1)

出典と根拠

ORDレコード
ord-505fcce30cf94159bb458b4de8d498b1
出典データセット
uspto-grants-2016_03
特許番号
US09296745B2

関連ノート

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