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

HRID 1769185

반응식

HRID 1769185 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 3411532-[(3-Chlorophenyl)thio]-5-methoxybenzoic acid수율 67.9%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
150 °C

실험 절차

To a mixture of 3-chlorothiophenol (20 g, 0.138 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.

후처리

  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

출처 및 근거

ORD 기록
ord-5954937a007e44a4a44183c074f0b0b5
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05380749

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