Triethylamine → 3-((4-(Difluoromethoxy)phenyl)ethynyl)phenol

HRID 30590ノート

反応式

HRID 30590 の反応式
[F:1][CH:2]([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][CH:5]=1.C(N(CC)CC)C.[OH:19][C:20]1[CH:21]=[C:22]([C:26]#[CH:27])[CH:23]=[CH:24][CH:25]=1.C(OCC)(=O)C>CN(C)C=O.[Cu](I)I>[F:1][CH:2]([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:27]#[C:26][C:22]2[CH:21]=[C:20]([OH:19])[CH:25]=[CH:24][CH:23]=2)=[CH:6][CH:5]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 139144m-EthynylphenolHCID 27370081-(Difluoromethoxy)-4-iodobenzene

生成物 1

HCID 597903213-((4-(Difluoromethoxy)phenyl)ethynyl)phenol

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4-(difluoromethoxy)phenyl iodide (4.70 g) in deoxygenated dimethylformamide was treated with trans-dichlorobis(triphenylphosphine) palladium(II) (244 mg) and copper(II) iodide 66 mg) followed by triethylamine (7.52 mL), stirred under a nitrogen atmosphere for 5min., treated with 3-hydroxyphenyl acetylene (2.467 g), stirred under nitrogen atmosphere for 16 h, poured into ethyl acetate and was washed with 0.05 N HCl and water. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was chromatographed, silica gel, 40% ethyl acetate/hexane as eluent, to afford 3-((4-(difluoromethoxy)phenyl)ethynyl)phenol as a tan solid, 5.40 g; 1H NMR (DMSO-d6): δ 9.64 (s, 1H), 7.56 (d, J=8.8 Hz, 2H), 7.27 (t, J=73.7 Hz, 1H), 7.17 (d, J=8.8 Hz, 2H), 7.16 (m, 1H), 6.94 (m, 1H), 6.86 (m, 1H), and 6.77 (m, 1H); MS (ES neg) m/z 260.

後処理

  1. stirringstirred under nitrogen atmosphere for 16 h
  2. washwas washed with 0.05 N HCl and water
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed

出典と根拠

ORDレコード
ord-d89ce363547847d1ae42f1a34706a5ac
出典データセット
uspto-grants-2008_09
特許番号
US07423158B2

反応ノート

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