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

HRID 547856ノート

反応式

HRID 547856 の反応式
[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

参加物

6

反応物 3

HCID 702Ethanol2 回HCID 25517Ammonium ChlorideHCID 582877964,5-Difluoro-2-methoxy-4'-(3-nitro-benzyloxy)-biphenyl

生成物 1

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

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8857Ethyl Acetate溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-baf8d7e209eb4964b45ff242e4c07293
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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