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Water → 2'-Fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-ol

HRID 1049400
Notes
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Reaction equation

HRID 1049400 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[C:28]1[CH:33]=[CH:32][C:31]([O:34][Si](C(C)C)(C(C)C)C(C)C)=[CH:30][C:29]=1[CH2:45][C:46]([CH3:49])([CH3:48])[CH3:47].O>C1COCC1>[F:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][C:29]=1[CH2:45][C:46]([CH3:49])([CH3:48])[CH3:47]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 131736007((2'-Fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)oxy)triisopropylsilane

Product 1

HCID 1177596322'-Fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.0M solution of tetrabutylammonium fluoride in THF (73.6 mL) was added to a solution of ((2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-yl)oxy)triisopropylsilane (total amount) obtained in Example 2, step F, in THF (30 mL) at room temperature, and the mixture was stirred for 15 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (8.68 g) as a pale-yellow amorphous solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8378ce5ce19c4c35999e5591177a69be
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09382188B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes