1-Bromo-3-chloropropane → HCID 86709383, compound

HRID 2172210Notes

Reaction equation

HRID 2172210 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].[F:6][C:7]([F:17])([F:16])[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[Cl:5][CH2:4][CH2:3][CH2:2][O:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:7]([F:6])([F:16])[F:17])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 70015p-(Trifluoromethoxy)phenol

Product 1

HCID 86709383HCID 86709383, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1-Bromo-3-chloropropane (2.37 ml, 24 mmol), 4-(trifluoromethoxy)phenol (3.56 g, 20 mmol) and potassium carbonate (4.15 g, 30 mmol) were stirred in NMP (30 ml) overnight. After removing potassium carbonate by filtration, water was added to the mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and dried over sodium sulfate. The solvent was distilled off, and the residue was fractionated and purified by silica gel column chromatography (hexane:ethyl acetate=89:11) to afford the title compound as a colorless oil (5.09 g, yield 99%).

Workup

  1. customAfter removing potassium carbonate
  2. filtrationby filtration, water
  3. additionwas added to the mixture
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent was distilled off
  8. custompurified by silica gel column chromatography (hexane:ethyl acetate=89:11)

Sources & evidence

ORD record
ord-15de6ca750fd47a2927b51c37d5715e7
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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