Potassium Hydroxide → HCID 58046304, compound

HRID 2359299Notes

Reaction equation

HRID 2359299 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#N)=[C:9]([O:15][CH3:16])[CH:8]=2)=[C:4]([O:19][C:20]([F:23])([F:22])[F:21])[CH:3]=1.[OH-:24].[K+].C(O)CO.[OH2:30]>>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]([OH:30])=[O:24])=[C:9]([O:15][CH3:16])[CH:8]=2)=[C:4]([O:19][C:20]([F:23])([F:22])[F:21])[CH:3]=1

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 20437942Ethylene glycol waterHCID 66666430HCID 66666430, compound

Product 1

HCID 58046304HCID 58046304, compound

Conditions

Temperature
120 °C

Procedure

To a solution of 4-[4-chloro-2-(trifluoromethoxy)phenoxy]-2-methoxybenzonitrile (Preparation 103, 230 mg, 0.66 mmol) in 10 mL of ethylene glycol/water (8:2) was added KOH flakes (380 mg, 6.6 mmol). The reaction mixture was heated to 120° C. for 64 hours. After cooling to room temperature the residue was partitioned between EtOAc (80 mL) and water (75 mL), the aqueous layer was separated, acidified with 2M HCl and extracted with EtOAc (2×50 mL). The organic layers were combined, dried over MgSO4 and evaporated in vacuo to yield 167 mg of the title compound as yellow oil.

Workup

  1. temperatureAfter cooling to room temperature the residue
  2. customwas partitioned between EtOAc (80 mL) and water (75 mL)
  3. customthe aqueous layer was separated
  4. extractionextracted with EtOAc (2×50 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-ad28e4d73a2141eb922ef5c15fee5640
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

Loading…