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

HRID 547856Notes

Reaction equation

HRID 547856 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-baf8d7e209eb4964b45ff242e4c07293
Source dataset
uspto-grants-2011_05
Patent number
US07939569B1

Reaction notes

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