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

HRID 270008ノート

反応式

HRID 270008 の反応式
[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

参加物

3

反応物 1

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

生成物 1

HCID 113097545-Chlorobenzo(b)thiophene収率 32%

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-1d483973104543e6891924d78d2d4829
出典データセット
uspto-grants-2008_11
特許番号
US07449481B2

反応ノート

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