Water → HCID 89619235, compound

HRID 1525669Notes

Reaction equation

HRID 1525669 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]1[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=1.O>CS(C)=O.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:20][C:21]2[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=2)=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 805204-Chloro-3-(trifluoromethyl)phenolHCID 954261Ethyl 4-(bromomethyl)benzoate

Product 1

HCID 89619235HCID 89619235, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-chloro-3-(trifluoromethyl)phenol (190 mg, 0.97 mmol) in DMSO (5.0 mL) was added potassium carbonate (276 mg, 2.0 mmol). The reaction mixture was stirred at room temperature for 10 minutes, before addition of ethyl 4-(bromomethyl)benzoate (235 mg, 0.97 mmol). The resulting mixture was heated to 70° C. with stirring for 3 hours before cooling back to room temperature. Water (50 mL) and EtOAc (50 mL) were added and the layers partitioned. The aqueous fractions were washed with EtOAc (2×50 mL) and the combined organic layers dried over magnesium sulfate, filtered and concentrated in vacuo to yield a white solid as the title compound (350 mg, 100%).

Workup

  1. temperaturebefore cooling back to room temperature
  2. customthe layers partitioned
  3. washThe aqueous fractions were washed with EtOAc (2×50 mL)
  4. dry with materialthe combined organic layers dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7048832b45a46aebad2b4249e3d2b9d
Source dataset
uspto-grants-2015_07
Patent number
US09085517B2

Reaction notes

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