Water → HCID 58278769, compound

HRID 85171

Reaction equation

HRID 85171 reaction equation
Cl[CH2:2][C@H:3]1[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[O:4]1.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=1[C:18]([F:21])([F:20])[F:19].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:2][C@H:3]2[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[O:4]2)=[CH:13][C:12]=1[C:18]([F:19])([F:20])[F:21]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2734443(R)-(+)-4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolaneHCID 222773074-Bromo-3-(trifluoromethyl)phenol

Product 1

HCID 58278769HCID 58278769, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

(S)-4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane (63; 3.3 g, 20.5 mmol) was added to a mixture containing 4-bromo-3-(trifluoromethyl)phenol (126; 5 g, 20 mmol) and K2CO3 (8.30 g, 60 mmol) in 20 mL of DMF. The resulting reaction mixture was stirred at 60° C. for 6 h. Upon cooling to room temperature, the mixture was poured into water and extracted by EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (petroleum ether:EtOAc=50:1) to afford (S)-4-((4-bromo-3-(trifluoromethyl)phenoxy)methyl)-2,2-dimethyl-1,3-dioxolane (4 g, 56%).

Workup

  1. customThe resulting reaction mixture
  2. temperatureUpon cooling to room temperature
  3. extractionextracted by EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by chromatography (petroleum ether:EtOAc=50:1)

Sources & evidence

ORD record
ord-99307bbd987049a580407d3592273530
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Linked notes

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