Isopropanol → HCID 58404446, compound

HRID 1942583Notes

Reaction equation

HRID 1942583 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[CH3:14][CH:15]([OH:17])[CH3:16].[H-].[Na+]>O1CCCC1>[CH3:14][CH:15]([O:17][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11])[CH3:16]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 1442554-Fluoro-3-(trifluoromethyl)benzonitrile

Product 1

HCID 58404446HCID 58404446, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 4-fluoro-3-(trifluoromethyl)benzonitrile (10 g), i-PrOH (8.15 mL) in tetrahydrofuran (THF) (90 mL) stirred under nitrogen at −10° C. was added solid NaH (3.46 g) portionwise during 30 min. The reaction mixture was stirred at −10° C. for 6 h. The reaction mixture was quenched with water, partitioned between ether (100 mL) and water (50 mL). The organic phase was dried over magnesium sulphate and evaporated in vacuo to give the crude product 4-[(1-methylethyl)oxy]-3-(trifluoromethyl)benzonitrile (D10) (15 g).

Workup

  1. customThe reaction mixture was quenched with water
  2. custompartitioned between ether (100 mL) and water (50 mL)
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-012129b40fcc43a78051dac56f5f4c69
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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