Ozone → 2-Fluoro-4-(hydroxymethyl)benzonitrile

HRID 1717490Notes

Reaction equation

HRID 1717490 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH:10]=C)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[O:12]=[O+][O-].[BH4-].[Na+]>C(Cl)Cl.CO>[F:1][C:2]1[CH:9]=[C:8]([CH2:10][OH:12])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 219046072-Fluoro-4-vinylbenzonitrile

Product 1

HCID 118296312-Fluoro-4-(hydroxymethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Into a cooled solution (−78° C.) of 2-fluoro-4-vinylbenzonitrile (1.3 g, 8.8 mmol; see step (i) above) in 40 mL of CH2Cl2 and 5 mL of methanol was bubbled ozone (50 L/h, 29 g/m3) for 30 min. Argon was subsequently bubbled through to remove excess ozone. Sodium borohydride (0.67 g, 0.018 mol) was added and the cooling bath was removed. The mixture was stirred and allowed to react for 1 h. The mixture was evaporated and 2M HCl was added. The mixture was extracted twice with diethyl ether and the combined ether fraction was dried (Na2SO4) and evaporated. The crude product crystallised. Yield: 1.1 g (81%).

Workup

  1. customArgon was subsequently bubbled through
  2. customto remove excess ozone
  3. customthe cooling bath was removed
  4. customto react for 1 h
  5. customThe mixture was evaporated
  6. addition2M HCl was added
  7. extractionThe mixture was extracted twice with diethyl ether
  8. dry with materialthe combined ether fraction was dried (Na2SO4)
  9. customevaporated
  10. customThe crude product crystallised

Sources & evidence

ORD record
ord-7b86e22a73864fe5a134a57b692e586b
Source dataset
uspto-grants-2010_09
Patent number
US07803954B2

Reaction notes

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