Sodium Carbonate → (1S)-2,2-difluoro-1-(3'-fluoro-5'-nitrobiphenyl-4-yl)ethanol

HRID 530397ノート

反応式

HRID 530397 の反応式
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4](I)[CH:3]=1.[F:12][CH:13]([F:25])[C@H:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)[OH:15].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[F:12][CH:13]([F:25])[C@H:14]([C:16]1[CH:17]=[CH:18][C:19]([C:4]2[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([F:1])[CH:3]=2)=[CH:20][CH:21]=1)[OH:15]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 2590861-Fluoro-3-iodo-5-nitrobenzeneHCID 129321750{4-[(1S)-2,2-difluoro-1-hydroxyethyl]phenyl}boronic acid

生成物 1

HCID 118307555(1S)-2,2-difluoro-1-(3'-fluoro-5'-nitrobiphenyl-4-yl)ethanol

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

A mixture of PdCl2 (dppf)—dichloromethane adduct (40.8 mg, 0.050 mmol), 1-fluoro-3-iodo-5-nitrobenzene (267 mg, 1.00 mmol), {4-[(1S)-2,2-difluoro-1-hydroxyethyl]phenyl}boronic acid (222 mg, 1.10 mmol), sodium carbonate (1.50 mL, 3.00 mmol) and DMF (5 mL) was degassed by sparging with nitrogen and then heated to 85° C. for 3 hours. Upon cooling to room temperature, the reaction mixture was diluted with water, and aqueous NH4Cl, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes) to give (1S)-2,2-difluoro-1-(3′-fluoro-5′-nitrobiphenyl-4-yl)ethanol. MS ESI calc'd. for C14H11F3NO3[M+H]+ 298, found 298.

後処理

  1. customwas degassed
  2. customby sparging with nitrogen
  3. temperatureUpon cooling to room temperature
  4. additionthe reaction mixture was diluted with water, and aqueous NH4Cl
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-52bb75690a4e4006bb602cf7016a4353
出典データセット
uspto-grants-2016_05
特許番号
US09353066B2

反応ノート

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