Triphenylphosphine → 4-(Bromomethyl)picolinonitrile

HRID 619855Notes

Reaction equation

HRID 619855 reaction equation
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:22]([C:24]1[CH:29]=[C:28]([CH2:30]O)[CH:27]=[CH:26][N:25]=1)#[N:23]>C(Cl)Cl>[C:22]([C:24]1[CH:29]=[C:28]([CH2:30][Br:1])[CH:27]=[CH:26][N:25]=1)#[N:23]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 107253914-(Hydroxymethyl)pyridine-2-carbonitrile

Product 1

HCID 106317764-(Bromomethyl)picolinonitrileYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Bromine (6.88 g, 43.1 mmol) is added dropwise to a solution of triphenylphosphine (11.3 g, 43.1 mmol) in 280 mL of CH2Cl2 at 0° C. The mixture is tirred for 30 minutes at 0° C. At this time, 2-cyano-4-(hydroxymethyl)-pyridine (4.82 g, 35.9 mmol) is added and the resulting mixture is stirred for 2 hours at room temperature. The reaction mixture is diluted with CH2Cl2 and washed with water (2x) and saturated NaCl solution. The organic layer is dried with MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting in a gradient of 20% EtOAc/hexanes to 30% EtOAc/hexanes to afford the title compound (6.40 g, 32.5 mmol) as an oil.

Workup

  1. washwashed with water (2x) and saturated NaCl solution
  2. dry with materialThe organic layer is dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by column chromatography
  6. washeluting in a gradient of 20% EtOAc/hexanes to 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-2588eef75cfc4e2e94f71ede74c68103
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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