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Hydrochloric Acid → 1-(4-Amino-3,5-dimethyl-phenyl)-2,2,2-trifluoro-1-(4-fluorophenyl)-ethanol

HRID 1917053
Notes
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Reaction equation

HRID 1917053 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([N:12]([Si](C)(C)C)[Si](C)(C)C)=[C:7]([CH3:21])[CH:6]=1)[OH:4].Cl.[OH-].[Na+]>O1CCCC1>[NH2:12][C:8]1[C:9]([CH3:11])=[CH:10][C:5]([C:3]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)([OH:4])[C:2]([F:1])([F:29])[F:30])=[CH:6][C:7]=1[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 594978232,2,2-Trifluoro-1-(4-fluoro-phenyl)-1-[4-(1,1,1,3,3,3-hexamethyl disilazan-2-yl)-3,5-dimethyl-phenyl]-ethanol

Product 1

HCID 594978191-(4-Amino-3,5-dimethyl-phenyl)-2,2,2-trifluoro-1-(4-fluorophenyl)-ethanol

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2,2,2-trifluoro-1-(4-fluoro-phenyl)-1-[4-(1,1,1,3,3,3-hexamethyl disilazan-2-yl)-3,5-dimethyl-phenyl]-ethanol (Example I2) (5 mmol) in tetrahydrofuran (15 ml) was added aqueous hydrochloric acid (concentrated) (1 ml) at 20° C. The reaction mixture was stirred at 20° C. for 15 hours. The reaction mixture was neutralized by addition of aqueous sodium hydroxide (4M). The mixture was extracted with diethyl ether. The organic phase was dried over sodium sulfate, filtered through a plug of silica gel and concentrated. The residue was triturated with heptane and a small amount of diethyl ether, then filtered and dried. The title compound was isolated as off-white crystals.

Workup

  1. customat 20° C
  2. extractionThe mixture was extracted with diethyl ether
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered through a plug of silica gel
  5. concentrationconcentrated
  6. customThe residue was triturated with heptane
  7. filtrationa small amount of diethyl ether, then filtered
  8. customdried

Sources & evidence

ORD record
ord-73cadd65aa904144928d79a4b7175d74
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08618173B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes