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

HRID 2181553ノート

反応式

HRID 2181553 の反応式
[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]

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 311Citric Acid溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1a70e53bb5074c6e80593a27b084e3e2
出典データセット
uspto-grants-2005_05
特許番号
US06891044B2

反応ノート

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