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

HRID 1861116ノート

反応式

HRID 1861116 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, H), 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-04861ba9de7e4ea6af0286bc035ae813
出典データセット
uspto-grants-2003_03
特許番号
US06531491B1

反応ノート

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