Sodium Bicarbonate → HCID 67107891, 화합물

HRID 2177752노트

반응식

HRID 2177752 반응식
[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]

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 236662204-fluorobenzenesulfinic acid sodium saltHCID 67107500HCID 67107500, 화합물2회

생성물 1

HCID 67107891HCID 67107891, 화합물수율 81.8%

시약·촉매·용매 2

HCID 962Water용매2회HCID 31374Dimethylacetamide용매

실험 절차

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.

후처리

  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%

출처 및 근거

ORD 기록
ord-93225c496d8f4338b8e5bda27bd12863
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067905B2

반응 노트

불러오는 중…