Hydrochloric Acid → HCID 67153485, compound

HRID 1914349Notes

Reaction equation

HRID 1914349 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([O:18][C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][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:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH:10]([C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:26])=[O:2])=[CH:9][CH:8]=2)[CH2:11][CH2:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[CH:24][CH:23]=1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 67153571HCID 67153571, compound

Product 1

HCID 67153485HCID 67153485, compoundYield 89.7%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Racemic 4-[1-(4-bromo-phenoxy)-5,5,5-trifluoro-pentyl]-benzoic acid methyl ester (7.80 g, 18.1 mmol) is dissolved in the tetrahydrofuran (75 mL) and sodium hydroxide (25 mL, 5N) is added. The reaction is heated to reflux under nitrogen. The reaction is monitored by HPLC, and upon complete conversion, the reaction is neutralized with hydrochloric acid (25 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 (7.46 g, 16.24 mmol) is used without further purification.

Workup

  1. additionis added
  2. temperatureThe reaction is heated
  3. temperatureto reflux under nitrogen
  4. customThe two phases are separated
  5. washthe organic layer is washed
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2dd6a446da814f8da60c38d6161dd99f
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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