Ethanol → 3-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-phenylamine

HRID 547856노트

반응식

HRID 547856 반응식
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=3)=[CH:11][CH:10]=2)=[C:4]([O:26][CH3:27])[CH:3]=1.C(O)C.[Cl-].[NH4+]>[Zn].C(OCC)(=O)C>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][C:17]3[CH:18]=[C:19]([NH2:23])[CH:20]=[CH:21][CH:22]=3)=[CH:13][CH:14]=2)=[C:4]([O:26][CH3:27])[CH:3]=1

참가 물질

6

반응물 3

HCID 702Ethanol2회HCID 25517Ammonium ChlorideHCID 582877964,5-Difluoro-2-methoxy-4'-(3-nitro-benzyloxy)-biphenyl

생성물 1

HCID 671537683-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-phenylamine수율 102.5%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 8857Ethyl Acetate용매

실험 절차

To a flask containing 4,5-difluoro-2-methoxy-4′-(3-nitro-benzyloxy)-biphenyl (1.49 g, 4.0 mmol) was added ethanol (40 ml), zinc (2.5 g, 40 mmol) and ammonium chloride (3.2 g, 60.2 mmol). Additional solvent was added over time, ethanol (30 mL at 15 min) and ethyl acetate (10 mL at 45 min). After 1 hr the reaction was filtered through Celite, concentrated, diluted with ethyl acetate (100 mL), washed with saturated aqueous sodium bicarbonate (200 mL) and brine (100 mL), dried over magnesium sulfate, concentrated and dried from hexanes/methylene chloride mixtures to yield 3-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-phenylamine as a yellow oil (1.4 g, 100%). LC-MS (ES) calculated for C20H17F2NO2, 341.12; found m/z 342 [M+H]+.

후처리

  1. filtrationAfter 1 hr the reaction was filtered through Celite
  2. concentrationconcentrated
  3. additiondiluted with ethyl acetate (100 mL)
  4. washwashed with saturated aqueous sodium bicarbonate (200 mL) and brine (100 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. dry with materialdried from hexanes/methylene chloride

출처 및 근거

ORD 기록
ord-baf8d7e209eb4964b45ff242e4c07293
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939569B1

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