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

HRID 1990753Notes

Reaction equation

HRID 1990753 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].[BH4-].[Na+].C[OH:15]>C(Cl)Cl>[F:1][C:2]1[CH:9]=[C:8]([CH2:10][OH:15])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 219046072-Fluoro-4-vinylbenzonitrile

Product 1

HCID 118296312-Fluoro-4-(hydroxymethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 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 to 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. customto bubbled ozone (50 L/h, 29 g/m3) for 30 min
  2. customArgon was subsequently bubbled through
  3. customto remove excess ozone
  4. customthe cooling bath was removed
  5. customto react for 1 h
  6. customThe mixture was evaporated
  7. addition2M HCl was added
  8. extractionThe mixture was extracted twice with diethyl ether
  9. dry with materialthe combined ether fraction was dried (Na2SO4)
  10. customevaporated
  11. customThe crude product crystallised

Sources & evidence

ORD record
ord-6c5371c9a270416bbb22d298250a59c0
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

Loading…