Diethyl Ether → HCID 67970696、化合物

HRID 889530ノート

反応式

HRID 889530 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]([F:12])[F:11])[C:5]#[N:6].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C]=[O:50].C[CH2:52][O:53][CH2:54]C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C.CO>[C:5]([C:4]1[CH:7]=[CH:8][C:9]([CH:10]([F:12])[F:11])=[C:2]([CH:3]=1)[C:52]([O:53][CH3:54])=[O:50])#[N:6]

参加物

9

反応物 5

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 67970619HCID 67970619、化合物HCID 178418416HCID 178418416、化合物

生成物 1

HCID 67970696HCID 67970696、化合物収率 77%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

Purge a mixture of 3-bromo-4-(difluoromethyl)benzonitrile (8.87 g, 38.2 mmol, 1.0 equiv), triethylamine (16.0 mL, 114.7 mmol, 3.0 equiv), methanol (70 mL), and DMF (120 mL) with nitrogen, then treat the mixture with palladium(II) acetate (867 mg, 3.82 mmol, 0.1 equiv) and 1,3-bis(diphenylphosphino)propane (1.61 g, 3.82 mmol, 0.1 equiv). Stir the mixture under 138 kPaG of carbon monoxide at room temperature for two days and then 80° C. for one day. Cool the mixture to room temperature and dilute with Et2O (300 mL). Wash the mixture with water and saturated aqueous NaCl, and separate the organic layer. Dry the organic layer over sodium sulfate, filter, and concentrate under reduced pressure. Subject the resulting crude material to chromatography on silica gel eluting with a 10-15% THF/hexanes gradient to give the title compound (6.19 g, 77%). GC/MS (m/z) 211 (M).

後処理

  1. customPurge
  2. washWash the mixture with water and saturated aqueous NaCl
  3. customseparate the organic layer
  4. dry with materialDry the organic layer over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

出典と根拠

ORDレコード
ord-3b0c2e1bd6874a07b3738ffadebf457b
出典データセット
uspto-grants-2012_08
特許番号
US08252831B2

反応ノート

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