1,3-Difluoro-2-propanol → 3-(2-Fluoro-1-fluoromethyl-ethoxy)-4-nitro-benzonitrile

HRID 532273Notes

Reaction equation

HRID 532273 reaction equation
[F:1][CH2:2][CH:3]([OH:6])[CH2:4][F:5].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.F[C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[N+:26]([O-:28])=[O:27])[C:21]#[N:22]>C1COCC1.O>[F:1][CH2:2][CH:3]([CH2:4][F:5])[O:6][C:24]1[CH:23]=[C:20]([CH:19]=[CH:18][C:25]=1[N+:26]([O-:28])=[O:27])[C:21]#[N:22]

Participants

6

Reactant 3

HCID 679851,3-Difluoro-2-propanolHCID 2733832Lithium HexamethyldisilazideHCID 27833993-Fluoro-4-nitrobenzonitrile

Product 1

HCID 584133843-(2-Fluoro-1-fluoromethyl-ethoxy)-4-nitro-benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1,3-Difluoro-propan-2-ol (4.2 g) was dissolved under argon in THF (250 ml) and cooled to 0° C. LiHMDS (28 ml) was added to the mixture and stirred at rt for 1 hour. Then the mixture was cooled to 0° C. and 3-fluoro-4-nitrobenzonitrile (1.95 ml) was added in portions and stirred for 2 hours. The mixture was poured in water and extracted with DCM. The organic layer was washed with water, dried and concentrated.

Workup

  1. temperatureThen the mixture was cooled to 0° C.
  2. stirringstirred for 2 hours
  3. extractionextracted with DCM
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4b72932b3cb84c42ac26ae000d7ed6bb
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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