Tetrabutylammonium Fluoride → (4-Fluoro-3,5-diisopropoxyphenyl)methanol

HRID 62773Notes

Reaction equation

HRID 62773 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([Si]([O:26][CH2:27][C:28]1[CH:33]=[C:32]([O:34][CH:35]([CH3:37])[CH3:36])[C:31]([F:38])=[C:30]([O:39][CH:40]([CH3:42])[CH3:41])[CH:29]=1)(C)C)(C)(C)C>C1COCC1>[F:38][C:31]1[C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[CH:33][C:28]([CH2:27][OH:26])=[CH:29][C:30]=1[O:39][CH:40]([CH3:42])[CH3:41]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67041823tert-Butyl(4-fluoro-3,5-diisopropoxybenzyloxy)dimethylsilane

Product 1

HCID 67041705(4-Fluoro-3,5-diisopropoxyphenyl)methanolYield 116.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF) (1.35 mL, 1.35 mmol) was added to a solution of tert-butyl(4-fluoro-3,5-diisopropoxybenzyloxy)dimethylsilane (6) (600 mg, 1.35 mmol) in THF at 0° C. and the mixture was stirred at this temperature for 1 h. The mixture was partitioned between NH4Cl (satd. aq.) (50 mL) and EtOAc (100 mL). The phases were separated and the organic solution was washed with brine (50 mL), then dried over MgSO4 and filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (40 g, 0-50% EtOAc in isohexane) to afford (4-fluoro-3,5-diisopropoxyphenyl)methanol (7) (382 mg, 100%) as a colourless oil.

Workup

  1. customThe mixture was partitioned between NH4Cl (satd. aq.) (50 mL) and EtOAc (100 mL)
  2. customThe phases were separated
  3. washthe organic solution was washed with brine (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by silica gel chromatography (40 g, 0-50% EtOAc in isohexane)

Sources & evidence

ORD record
ord-8ac8f2fcf53c4b29a080071df32350e6
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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