Methanol → 2,4-Difluoro-3-[[3-fluoro-5-(3-fluorophenyl)-2-methy-phenyl]methylamino]phenol

HRID 1771731Notes

Reaction equation

HRID 1771731 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[NH:10][C:11](=O)[C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)[CH:15]=[C:14]([F:25])[C:13]=1[CH3:26].CO>C1COCC1>[F:1][C:2]1[C:3]([NH:10][CH2:11][C:12]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)[CH:15]=[C:14]([F:25])[C:13]=2[CH3:26])=[C:4]([F:9])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 887MethanolHCID 89444441HCID 89444441, compound

Product 1

HCID 894437892,4-Difluoro-3-[[3-fluoro-5-(3-fluorophenyl)-2-methy-phenyl]methylamino]phenolYield 103.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-(2,6-difluoro-3-hydroxy-phenyl)-3-fluoro-5-(3-fluorophenyl)-2-methyl-benzamide (0.9 g, 2.4 mmol, 1.0 eq) in THF (20 mL) under N2 was added a solution of BH3 (1 M in THF, 11.9 mL, 11.9 mmol, 5.0 eq). The reaction mixture was heated at reflux overnight. Methanol was added to quench the reaction and the solution was then concentrated in vacuo to give the title compound (900 mg, 100%) which was used without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. customto quench
  4. customthe reaction
  5. concentrationthe solution was then concentrated in vacuo

Sources & evidence

ORD record
ord-bdff69964f4e4167b870aa12c44af410
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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