1-Chloro-4-[(2,2-dimethoxyethyl)sulfanyl]benzene → 5-Chlorobenzo(b)thiophene

HRID 270008노트

반응식

HRID 270008 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH:10](OC)OC)=[CH:4][CH:3]=1>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[S:8][CH:9]=[CH:10][C:4]=2[CH:3]=1

참가 물질

3

반응물 1

HCID 141757591-Chloro-4-[(2,2-dimethoxyethyl)sulfanyl]benzene

생성물 1

HCID 113097545-Chlorobenzo(b)thiophene수율 32%

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

실험 절차

A mixture of polyphosphoric acid (11.2 g) in chlorobenzene (290 mL) was heated to reflux and added, under nitrogen, dropwise in about one hour 1-chloro-4-(2,2-dimethoxy-ethylsulfanyl)-benzene (compound PRE9; 9.12 g, 39.2 mmol). The reaction mixture was then heated for one night until reaction is complete, cooled, quenched with water (150 mL) and extracted into methylene chloride (200 mL). Combined organic layer was dried over Na2SO4 and concentrated to give a crude residue that was purified by flash chromatography (silica, eluting solvent: petroleum ether) to give 2.1 g of 5-chloro-benzo[b]thiophene (limpid oil) (Yield=32%).

후처리

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was then heated for one night until reaction
  4. temperaturecooled
  5. customquenched with water (150 mL)
  6. extractionextracted into methylene chloride (200 mL)
  7. dry with materialCombined organic layer was dried over Na2SO4
  8. concentrationconcentrated
  9. customto give a crude residue that
  10. customwas purified by flash chromatography (silica, eluting solvent: petroleum ether)

출처 및 근거

ORD 기록
ord-1d483973104543e6891924d78d2d4829
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449481B2

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