Potassium Carbonate → 2,5-Difluoro-4-[4-chloro-3-(trifluoromethyl)phenylmethoxy]-benzonitrile

HRID 508446Notes

Reaction equation

HRID 508446 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[F:14][C:15]1[CH:22]=[C:21](F)[C:20]([F:24])=[CH:19][C:16]=1[C:17]#[N:18].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[F:14][C:15]1[CH:22]=[C:21]([O:7][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([Cl:1])=[C:3]([C:10]([F:11])([F:12])[F:13])[CH:4]=2)[C:20]([F:24])=[CH:19][C:16]=1[C:17]#[N:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5938132,4,5-TrifluorobenzonitrileHCID 27781114-Chloro-3-(trifluoromethyl)benzyl alcohol

Product 1

HCID 866825572,5-Difluoro-4-[4-chloro-3-(trifluoromethyl)phenylmethoxy]-benzonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-chloro-3-(trifluoromethyl)-benzylalcohol (0.27 g, 1.28 mmol) and 2,4,5-trifluorobenzonitrile (0.2 g, 1.28 mmol) in DMSO (5 mL) was added potassium carbonate (0.33 g, 0.25 mmol). The resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was partitioned between water (15 mL) and EtOAc (20 mL). The organic layer was separated, dried over magnesium sulphate, filtered and evaporated to yield the title compound (0.43 g, 97%).

Workup

  1. customThe reaction mixture was partitioned between water (15 mL) and EtOAc (20 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-97ecc8f7c6b84c2390c803a275b8b8e3
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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