Acetonitrile → 6-Bromo-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 572399

반응식

HRID 572399 반응식
[CH3:1][O:2][C:3](=[O:6])[CH2:4][SH:5].C(#N)C.[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[C:13](F)[CH:12]=1.C(OCC)(=O)C>CCCCCC>[CH3:1][O:2][C:3]([C:4]1[S:5][C:13]2[CH:12]=[C:11]([Br:10])[CH:18]=[CH:17][C:14]=2[CH:15]=1)=[O:6]

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 16907Methyl ThioglycolateHCID 1435174-Bromo-2-fluorobenzaldehyde

생성물 1

HCID 224740786-Bromo-benzo[b]thiophene-2-carboxylic acid methyl ester수율 90%

시약·촉매·용매 1

HCID 8058Hexane용매

반응 조건

온도
85 °C

실험 절차

TEA (1.29 g, 12.85 mmol) and mercapto-acetic acid methyl ester (1.14 g, 10.83 mmol) were added to acetonitrile (50 mL) previously purged with argon (10 minute). This was followed by the addition of 4-bromo-2-fluoro-benzaldehyde (2 g, 9.852 mmol) and the resulting mixture was heated to reflux at 85° C. overnight. The reaction was monitored by TLC (20% ethyl acetate in hexane). The reaction mixture was cooled, concentrated, basified with 10% NaOH solution and extracted with ethyl acetate to afford the crude product. Purification by column chromatography on silica gel (5% ethyl acetate in hexane) afforded 2.4 g of the product (90% yield).

후처리

  1. custompreviously purged with argon (10 minute)
  2. temperaturethe resulting mixture was heated
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated
  5. extractionextracted with ethyl acetate
  6. customto afford the crude product
  7. customPurification by column chromatography on silica gel (5% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-186542ce22ab474899cd0b1ec79ee476
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029399B2

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