toluene-4-sulfonic acid (S)-2-(3-bromophenyl)-2-fluoro-ethyl ester → 1-bromo-(S)-3-(1-fluoropent-4-en-1-yl)benzene

HRID 30603ノート

反応式

HRID 30603 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C@H:8]([F:21])[CH2:9]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:5]=[CH:6][CH:7]=1.[CH2:22]([Mg]Br)[CH:23]=[CH2:24]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C@@H:8]([F:21])[CH2:9][CH2:24][CH:23]=[CH2:22])[CH:3]=1

参加物

4

反応物 2

HCID 59790335toluene-4-sulfonic acid (S)-2-(3-bromophenyl)-2-fluoro-ethyl esterHCID 178455850HCID 178455850、化合物

生成物 1

HCID 686490871-bromo-(S)-3-(1-fluoropent-4-en-1-yl)benzene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of toluene-4-sulfonic acid (S)-2-(3-bromophenyl)-2-fluoro-ethyl ester (5 mmol) in THF at room temperature is treated dropwise with a 1M solution of allylmagnesium bromide, stirred at room temperature for 5 h, quenched with saturated NH4Cl and extracted with ethyl acetate. The extracts are combined, washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to afford 1-bromo-(S)-3-(1-fluoropent-4-en-1-yl)benzene.

後処理

  1. customquenched with saturated NH4Cl
  2. extractionextracted with ethyl acetate
  3. washwashed sequentially with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e5904cd7f23f453db929e9aa454f32c8
出典データセット
uspto-grants-2008_09
特許番号
US07423158B2

反応ノート

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