(4'-(Benzyloxy)-4-fluoro-2',6'-dimethylbiphenyl-3-yl)methanol → 4'-Fluoro-3'-(hydroxymethyl)-2,6-dimethylbiphenyl-4-ol

HRID 2280671Notes

Reaction equation

HRID 2280671 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([CH2:23][OH:24])[CH:17]=2)=[C:11]([CH3:25])[CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:12]2[C:13]([CH3:15])=[CH:14][C:9]([OH:8])=[CH:10][C:11]=2[CH3:25])=[CH:17][C:18]=1[CH2:23][OH:24]

Participants

4

Reactant 1

HCID 89701768(4'-(Benzyloxy)-4-fluoro-2',6'-dimethylbiphenyl-3-yl)methanol

Product 1

HCID 897017694'-Fluoro-3'-(hydroxymethyl)-2,6-dimethylbiphenyl-4-olYield 83.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The crude (4′-(benzyloxy)-4-fluoro-2′,6′-dimethylbiphenyl-3-yl)methanol 18b (370 mg, 1.10 mmol) was dissolved in 5 mL of methanol, followed by addition of Pd/C (40 mg, 10%) under hydrogen atomosphere. The reaction mixture was stirred for 12 hours. The resulting mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography with elution system B to obtain the title compound 4′-fluoro-3′-(hydroxymethyl)-2,6-dimethylbiphenyl-4-ol 18c (225 mg, yield 83.3%) as a white solid.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography with elution system B

Sources & evidence

ORD record
ord-5cc8d5390ed34231869d2270b3fcc883
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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