Potassium Cyanide → HCID 90299189, compound

HRID 1749455Notes

Reaction equation

HRID 1749455 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[CH:4][C:3]=1[O:10][C:11]([F:14])([F:13])[F:12].[C-:15]#[N:16].[K+].C(=O)(O)[O-].[Na+]>CCO.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:15]#[N:16])=[CH:4][C:3]=1[O:10][C:11]([F:14])([F:13])[F:12]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 69673296HCID 69673296, compound

Product 1

HCID 90299189HCID 90299189, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1-bromo-4-(bromomethyl)-2-(trifluoromethoxy)benzene (1 g, 3.0 mmol) in EtOH (20 mL) and water (5 mL) was added potassiumcyanide (390 mg, 6 mmol). The resulting mixture was stirred at 85° C. for 2 h. Sodium bicarbonate was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to afford the crude title product (800 mg, 2.86 mmol). MS (ESI) m/z 279.9 M+, 281.1 [M+2]+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3cf70d4a3dc34f83a0da596669d9cf24
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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