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

HRID 547855노트

반응식

HRID 547855 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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]−.

후처리

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

출처 및 근거

ORD 기록
ord-c20ab3bb1f724881b211dcb3746ed574
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939569B1

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