Dimethyl Sulfoxide → HCID 89544754, 화합물

HRID 2283389노트

반응식

HRID 2283389 반응식
Br[CH2:2][C:3]1[C:4]([F:18])=[C:5]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])[C:6]([Cl:9])=[CH:7][CH:8]=1.C(=O)(O)[O-:20].[Na+].CS(C)=O>C(OCC)(=O)C>[C:10]([C:5]1[C:4]([F:18])=[C:3]([CH:8]=[CH:7][C:6]=1[Cl:9])[CH:2]=[O:20])(=[O:11])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 516892Sodium BicarbonateHCID 89544688HCID 89544688, 화합물

생성물 1

HCID 89544754HCID 89544754, 화합물수율 90%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Step 3 A mixture of (3-bromomethyl-6-chloro-2-fluoro-phenyl)-phenyl-methanone (292 mg, 0.896 mmol), sodium bicarbonate (700 mg, 8.33 mmol) and dimethylsulfoxide (10 ml) was heated to 80 degC for 3 hours. The reaction mixture was then allowed to cool, ethyl acetate was added, and the mixture was washed with water, aqueous lithium chloride and brine before drying (MgSO4) and concentrating in vacuo. The residue was purified by silica chromatography eluting with 0-20% ethyl acetate/petroleum ether to furnish 3-benzoyl-4-chloro-2-fluoro-benzaldehyde (115 mg oil, 90% clean). 1H NMR (400 MHz, CDCl3): 10.34 (1H, s), 7.97 (1H, dd), 7.91-7.86 (2H, m), 7.72-7.67 (1H, m), 7.55 (2H, t), 7.44 (1H, d), 7.28 (1H, s). MS: [M+NH4]+ 280

후처리

  1. temperaturewas heated to 80 degC for 3 hours
  2. temperatureto cool
  3. washthe mixture was washed with water, aqueous lithium chloride and brine
  4. dry with materialbefore drying (MgSO4)
  5. concentrationconcentrating in vacuo
  6. customThe residue was purified by silica chromatography
  7. washeluting with 0-20% ethyl acetate/petroleum ether

출처 및 근거

ORD 기록
ord-4eb91cc340e64dcc933917224e2eece9
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145354B2

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