Hexane → 5-Bromo-3-methyl-1-benzothiophene

HRID 523552노트

반응식

HRID 523552 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10](=O)[CH3:11])=[CH:4][CH:3]=1.CCCCCC>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[S:8][CH:9]=[C:10]([CH3:11])[C:4]=2[CH:3]=1

참가 물질

4

반응물 2

HCID 8058HexaneHCID 8219021-((4-Bromophenyl)thio)propan-2-one

생성물 1

HCID 141757645-Bromo-3-methyl-1-benzothiophene수율 66%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

Polyphosphoric acid (7 g) was added to a solution of 1-(4-bromo-phenylsulfanyl)-propan-2-one (I-24a: 2.0 g, 8.163 mmol) in toluene (10 mL) and the resulting mixture was heated to 100° C. for 5 hours. The reaction was monitored by TLC (100% hexane). The reaction mixture was cooled to room temperature, quenched with ice, basified with potassium carbonate (pH˜8) and extracted with ethyl acetate. The organic layer was concentrated to yield the crude product. Purification by column chromatography on silica gel (100% hexane) afforded 1.2 g of product (66% yield)

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with ice
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated
  5. customto yield the crude product
  6. customPurification by column chromatography on silica gel (100% hexane)

출처 및 근거

ORD 기록
ord-571cedafd03f47918c816a7015a96622
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09339501B2

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