Sodium Sulfide → 3-Fluoro-2-mercapto-benzoic acid ethyl ester

HRID 2181553노트

반응식

HRID 2181553 반응식
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:6]=1F)[CH3:2].[S-2:14].[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:6]=1[SH:14])[CH3:2]

참가 물질

7

반응물 2

HCID 14804Sodium SulfideHCID 2761174Benzoic acid, 2,3-difluoro-, ethyl ester

생성물 1

HCID 229782253-Fluoro-2-mercapto-benzoic acid ethyl ester

시약·촉매·용매 4

HCID 311Citric Acid용매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of ethyl-2,3 difluorobenzoate (1.07 g, 5.75 mmol) in DMF (10 mL) was treated with sodium sulfide (896 mg, 11.5 mmol, 2.0 equiv) at 23° C. The mixture was stirred under argon for 10 h. The solution was diluted with ethyl acetate (50 mL) and water (50 mL) and 10% citric acid (5 mL). The organic layer was washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, decanted and concentrated under reduced pressure to give 3-Fluoro-2-mercapto-benzoic acid ethyl ester 1H NMR (300 MHz, CDCl3) δ 7.71 (t, 1H), 7.38 (m, 1H), 7.12 (m, 1H), 4.41 (q, 2H), 1.40 (t, 3H); LCMS (100% area) Rt=4.53 min, (pos) [M+H]/z Calc'd 201.0, found 200.9.

후처리

  1. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. customdecanted
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1a70e53bb5074c6e80593a27b084e3e2
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06891044B2

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