Sodium Bicarbonate → HCID 67107891、化合物

HRID 2177752ノート

反応式

HRID 2177752 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[Na+].[Br:12][C:13]1[C:14]([O:32][CH3:33])=[C:15]([C:21]([CH2:24]SC2C=CC=CC=2)=[CH:22][CH:23]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)(O)[O-].[Na+]>CC(N(C)C)=O.O>[Br:12][C:13]1[C:14]([O:32][CH3:33])=[C:15]([C:21]([CH2:24][S:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])=[CH:22][CH:23]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 236662204-fluorobenzenesulfinic acid sodium saltHCID 67107500HCID 67107500、化合物2 回

生成物 1

HCID 67107891HCID 67107891、化合物収率 81.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 31374Dimethylacetamide溶媒

実験手順

Sodium 4-fluorobenzenesulphinate (0.517 g) was added to a suspension of ethyl 3-bromo-6-bromomethyl-2-methoxybenzoate (Intermediate 87, 0.4 g) and sodium bicarbonate (0.24 g) in dimethylacetamide (8 ml) and water (2 ml) and the mixture was stirred at room temperature for 3 hours. The resultant mixture was diluted with water and loaded onto a C-18 SPE column. The column was flushed with water then eluted with DCM and ethyl acetate. The organic eluent was dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of t-butyl methyl ether and cyclohexane with a gradient of 0-60% to give ethyl 3-bromo-6-(4-fluorobenzenesulphonyl-methyl)-2-methoxybenzoate (0.37 g) as a colourless gum.

後処理

  1. customThe column was flushed with water
  2. washthen eluted with DCM and ethyl acetate
  3. dry with materialThe organic eluent was dried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica
  7. washeluting with a mixture of t-butyl methyl ether and cyclohexane with a gradient of 0-60%

出典と根拠

ORDレコード
ord-93225c496d8f4338b8e5bda27bd12863
出典データセット
uspto-grants-2015_06
特許番号
US09067905B2

反応ノート

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