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Hydrochloric Acid → HCID 131736006, compound

HRID 1049398
Notes
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Reaction equation

HRID 1049398 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:11]([OH:17])=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1.CC1C=CC=C(C)N=1.FC(F)(F)S(O[Si:32]([CH:39]([CH3:41])[CH3:40])([CH:36]([CH3:38])[CH3:37])[CH:33]([CH3:35])[CH3:34])(=O)=O.Cl>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:11]([OH:17])=[CH:12][C:13]([O:16][Si:32]([CH:39]([CH3:41])[CH3:40])([CH:36]([CH3:38])[CH3:37])[CH:33]([CH3:35])[CH3:34])=[CH:14][CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 117759897HCID 117759897, compound

Product 1

HCID 131736006HCID 131736006, compound

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Conditions

Temperature
-15 °C

Procedure

Under a nitrogen atmosphere, to a solution of 2′-fluoro-5′-methoxy-[1,1′-biphenyl]-2,4-diol (14.6 g) and 2,6-dimethylpyridine (10.2 mL) in toluene (100 mL) was added triisopropylsilyl trifluoromethanesulfonate (21.1 mL) at −15° C., and the mixture was stirred at −15° C. for 20 min. To the reaction mixture was added 1N hydrochloric acid, 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 as a white 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-f02931708b6348458d68392cf5616410
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09382188B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes