Sodium Carbonate → (1R)-1-(3',5'-dinitrobiphenyl-4-yl)-2,2-difluoroethanol

HRID 530400

反応式

HRID 530400 の反応式
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[F:14][CH:15]([F:27])[C@@H:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)[OH:17].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[N+:11]([C:4]1[CH:3]=[C:2]([C:21]2[CH:20]=[CH:19][C:18]([C@@H:16]([OH:17])[CH:15]([F:27])[F:14])=[CH:23][CH:22]=2)[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=1)([O-:13])=[O:12]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 445341-Bromo-3,5-dinitrobenzeneHCID 129321749{4-[(1R)-2,2-difluoro-1-hydroxyethyl]phenyl}boronic acid

生成物 1

HCID 118307608(1R)-1-(3',5'-dinitrobiphenyl-4-yl)-2,2-difluoroethanol

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

A mixture of 1-bromo-3,5-dinitrobenzene (5 g, 19.6 mmol), PdCl2(dppf)-dichloromethane adduct (0.802 g, 0.982 mmol), {4-[(1R)-2,2-difluoro-1-hydroxyethyl]phenyl}boronic acid (4.36 g, 21.6 mmol), and aqueous sodium carbonate (2 M, 29.5 mL, 58.9 mmol) in dioxane (65.6 mL) was degassed by sparging with nitrogen. The mixture was heated to 85° C. for 2 hours, and then allowed to cool to room temperature. The mixture was diluted with water, 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 (1R)-1-(3′,5′-dinitrobiphenyl-4-yl)-2,2-difluoroethanol as an off-white solid. MS ESI calc'd. for C14H9F2N2O4[M+H−H2O]+ 307, found 307.

後処理

  1. customwas degassed
  2. customby sparging with nitrogen
  3. temperatureto cool to room temperature
  4. additionThe mixture was diluted with water
  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-94b656cdf2a84dd1b49eb422c18933f2
出典データセット
uspto-grants-2016_05
特許番号
US09353066B2

関連ノート

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