Dimethylformamide → 2-[(3-Chlorophenyl)thio]-5-methoxybenzoic acid

HRID 1377790ノート

反応式

HRID 1377790 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+].Br[C:21]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:22]=1[C:23]([OH:25])=[O:24]>O>[Cl:1][C:2]1[CH:3]=[C:4]([S:8][C:21]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:22]=2[C:23]([OH:25])=[O:24])[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 162573-ChlorothiophenolHCID 899062-Bromo-5-methoxybenzoic acid

生成物 1

HCID 3411532-[(3-Chlorophenyl)thio]-5-methoxybenzoic acid収率 60.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
150 °C

実験手順

To a mixture of 3-chlorothiophenol (20 g, 138 mol), and cupric acetate (1.8 g) and DMF (200 mL) was added K2CO3 (23 g). The mixture was heated to 150° C. for 15-20 minutes, then 2-bromo-5-methoxybenzoic acid (35.8 g, 0.155 mol) was added in portions. The mixture was heated overnight, poured into water (600 mL), filtered and the filtrate was treated with charcoal, filtered and diluted with HCl. The resulting precipitate was collected by filtration, washed with water, and dried at 50° C. in vacuo over P2O5 to afford 27.6 g of 2-[(3-chlorophenyl)thio]-5-methoxybenzoic acid.

後処理

  1. temperatureThe mixture was heated overnight
  2. filtrationfiltered
  3. additionthe filtrate was treated with charcoal
  4. filtrationfiltered
  5. additiondiluted with HCl
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water
  8. dry with materialdried at 50° C. in vacuo over P2O5

出典と根拠

ORDレコード
ord-98b358748542462683cb693f06d3c324
出典データセット
uspto-grants-1997_09
特許番号
US05665760

反応ノート

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