Hydrochloric Acid → HCID 67153422, compound

HRID 1914345Notes

Reaction equation

HRID 1914345 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([S:18][C:19]2[CH:24]=[C:23]([CH3:25])[C:22]([Br:26])=[C:21]([CH3:27])[CH:20]=2)[CH2:11][CH2:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[CH:6][CH:5]=1.Cl>O1CCCC1.[OH-].[Na+].C(OCC)C.O>[Br:26][C:22]1[C:23]([CH3:25])=[CH:24][C:19]([S:18][CH:10]([C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:28])=[O:2])=[CH:9][CH:8]=2)[CH2:11][CH2:12][CH2:13][C:14]([F:16])([F:17])[F:15])=[CH:20][C:21]=1[CH3:27]

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 67153437HCID 67153437, compound

Product 1

HCID 67153422HCID 67153422, compoundYield 92.8%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Racemic 4-[1-(4-bromo-3,5-dimethyl-phenylsulfanyl)-5,5,5-trifluoro-pentyl]-benzoic acid methyl ester (0.424 g, 0.890 mmol) is dissolved in the tetrahydrofuran (2.5 mL) and sodium hydroxide (2.5 mL, 5N) is added. The reaction is monitored by HPLC, and upon complete conversion, the reaction is neutralized with hydrochloric acid (2.5 mL, 5N) and diluted with diethyl ether and water. The two phases are separated, and the organic layer is washed, dried, and concentrated. The title compound (0.380 g, 0.826 mmol) is used without further purification.

Workup

  1. additionis added
  2. customThe two phases are separated
  3. washthe organic layer is washed
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e36b33b761da4a3b8c1e3addcb39bbfe
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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