Hydrochloric Acid → (2,3-Difluoro-4-methylphenyl)methanol

HRID 1712136Notes

Reaction equation

HRID 1712136 reaction equation
C([Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([F:17])[C:11]=1[F:18])(C)C)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.Cl>C1COCC1>[F:18][C:11]1[C:12]([F:17])=[C:13]([CH3:16])[CH:14]=[CH:15][C:10]=1[CH2:9][OH:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 18550272Tert-butyl-(2,3-difluoro-4-methyl-benzyloxy)-dimethyl-silane

Product 1

HCID 2774146(2,3-Difluoro-4-methylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl-(2,3-difluoro-4-methyl-benzyloxy)-dimethyl-silane (6.5 g, 24 mmol) in THF (24 mL) was added tetrabutylammonium fluoride (24 mL of a 1M solution in THF, 24 mmol). After stirring at ambient temperature for 1 hour, the mixture was poured into water, acidified with 1M aqueous HCl, extracted 3× with ethyl acetate, and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (10:1 to 2:1 hexane-ethyl acetate), affording (2,3-Difluoro-4-methyl-phenyl)-methanol as a tight yellow oil.

Workup

  1. extractionextracted 3× with ethyl acetate
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (10:1 to 2:1 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-f352fa425b564cc88ff29ae1d0bb55e6
Source dataset
uspto-grants-2010_09
Patent number
US07790902B2

Reaction notes

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