Potassium Carbonate → HCID 67373911, compound

HRID 1678058Notes

Reaction equation

HRID 1678058 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1.[OH:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][C:20]#[N:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][O:14][C:15]2[CH:23]=[CH:22][C:18]([CH2:19][C:20]#[N:21])=[CH:17][CH:16]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 265484-Hydroxybenzyl cyanideHCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzene

Product 1

HCID 67373911HCID 67373911, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture of 4-(trifluoromethoxy)benzyl bromide (2.5 g, 10 mmol), 4-hydroxybenzyl cyanide (1.1 g, 8 mmol) and potassium carbonate (1.4 g, 10 mmol) in acetone (25 mL) was heated to reflux for 7 hours. The mixture was then diluted with H2O (100 mL) and extracted with EtOAc (2×150 mL). Organics portions were combined and washed with brine and then dried with Na2SO4. The mixture was then filtered and the solvent was removed in vacuo affording 2.5 g of crude product. Purification by flash chromatography eluting with 30 percent ether/pentane over silica gel yielded 2.2 g of a white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 7 hours
  3. extractionextracted with EtOAc (2×150 mL)
  4. washwashed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationThe mixture was then filtered
  7. customthe solvent was removed in vacuo
  8. customaffording 2.5 g of crude product
  9. customPurification by flash chromatography
  10. washeluting with 30 percent ether/pentane over silica gel

Sources & evidence

ORD record
ord-a8ed8fb708f344be85b7d31dacfcfbdb
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Reaction notes

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