Dimethyl Sulfoxide → HCID 89544754、化合物

HRID 2283389ノート

反応式

HRID 2283389 の反応式
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

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 516892Sodium BicarbonateHCID 89544688HCID 89544688、化合物

生成物 1

HCID 89544754HCID 89544754、化合物収率 90%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-4eb91cc340e64dcc933917224e2eece9
出典データセット
uspto-grants-2015_09
特許番号
US09145354B2

反応ノート

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