Dimethylformamide → 4,5-Difluoro-2-methoxy-4'-(3-nitro-benzyloxy)-biphenyl

HRID 547855ノート

反応式

HRID 547855 の反応式
CN(C=O)C.Br[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=1.[F:17][C:18]1[C:23]([F:24])=[CH:22][C:21]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[C:20]([O:32][CH3:33])[CH:19]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C(OCC)(=O)C>[F:17][C:18]1[C:23]([F:24])=[CH:22][C:21]([C:25]2[CH:26]=[CH:27][C:28]([O:31][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=3)=[CH:29][CH:30]=2)=[C:20]([O:32][CH3:33])[CH:19]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 2733832Lithium HexamethyldisilazideHCID 582599934',5'-Difluoro-2'-methoxy-biphenyl-4-ol

生成物 1

HCID 582877964,5-Difluoro-2-methoxy-4'-(3-nitro-benzyloxy)-biphenyl収率 96.2%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of DMF (5 ml), 1-bromomethyl-3-nitro-benzene (0.92 g, 4.2 mmol), and 4′,5′-difluoro-2′-methoxy-biphenyl-4-ol (1 g, 4.2 mmol) was added lithium bis(trimethylsilyl)amide (1M in THF, 4.4 ml). The reaction was stirred at room temperature overnight and was then diluted with ethyl acetate (200 mL), washed with water (200 mL), aqueous ammonium chloride (10%, 200 mL) and brine, dried over magnesium sulfate and concentrated to yield 4,5-difluoro-2-methoxy-4′-(3-nitro-benzyloxy)-biphenyl as yellow solid (1.5 g, 95%). LC-MS (ES) calculated for C20H15F2NO4, 371.1; found m/z 370 [M−H]−.

後処理

  1. washwashed with water (200 mL), aqueous ammonium chloride (10%, 200 mL) and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-c20ab3bb1f724881b211dcb3746ed574
出典データセット
uspto-grants-2011_05
特許番号
US07939569B1

反応ノート

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