Toluene → Methyl 3-fluoro-4-methylbenzoate

HRID 220768

反応式

HRID 220768 の反応式
S(Cl)(Cl)=O.[F:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:9]([OH:11])=[O:10].[C:16]1(C)C=CC=CC=1>>[CH3:16][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:14]([CH3:15])=[C:6]([F:5])[CH:7]=1

参加物

4

反応物 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 676873-Fluoro-p-toluic acid

生成物 1

HCID 18973767Methyl 3-fluoro-4-methylbenzoate収率 83%

実験手順

Thionyl chloride (9.62 g, 81 mmol) was added to a solution of 3-fluoro-4-methylbenzoic acid (5.0 g, 32.4 mmol) in toluene (50 ml). The mixture was stirred at room temperature for 1.5 h and heated at reflux for 3 h. The sol-vent was removed in vacuo and the residue was taken up in methanol (30 ml) and CH2Cl2 (30 ml) and stirred for 18 h. The mixture was evaporated in vacuo and the residue was taken up in EtOAc (50 ml), washed with saturated NaHCO3 solution (3×75 ml), dried and evaporated in vacuo to yield the title compound (4.5 g, 83%).

後処理

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customThe sol-vent was removed in vacuo
  4. stirringCH2Cl2 (30 ml) and stirred for 18 h
  5. customThe mixture was evaporated in vacuo
  6. washwashed with saturated NaHCO3 solution (3×75 ml)
  7. customdried
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-a92516418eb34081835e188e8b1ab188
出典データセット
uspto-grants-2012_06
特許番号
US08202858B2

関連ノート

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