Acetone → 3-Bromomethyl-6-(2,6-diethyl-phenyl)-4-methoxy-pyridine-2-carbonitrile

HRID 1392627Notes

Reaction equation

HRID 1392627 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[N:16]=[C:15]([C:17]#[N:18])[C:14]([CH2:19]O[Si](C)(C)C)=[C:13]([O:25][CH3:26])[CH:12]=1)[CH3:2].C(Br)(Br)(Br)[Br:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)=O>CC#N.CCOCC.O>[Br:28][CH2:19][C:14]1[C:15]([C:17]#[N:18])=[N:16][C:11]([C:4]2[C:3]([CH2:1][CH3:2])=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:9][CH3:10])=[CH:12][C:13]=1[O:25][CH3:26]

Participants

8

Reactant 4

HCID 180AcetoneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 596783426-(2,6-Diethyl-phenyl)-4-methoxy-3-trimethylsilanyloxy methyl-pyridine-2-carbonitrile

Product 1

HCID 669943133-Bromomethyl-6-(2,6-diethyl-phenyl)-4-methoxy-pyridine-2-carbonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 6-(2,6-diethyl-phenyl)-4-methoxy-3-trimethylsilanyloxy methyl-pyridine-2-carbonitrile (200 mg, 0.54 mmol) in CH3CN (5 mL) is treated with CBr4 (270 mg, 0.81 mmol) and triphenylphosphine (215 mg, 0.81 mmol) at 0° C. under nitrogen. After one hour, acetone (50 mg) is added and the resulting mixture is stirred at room temperature overnight. Water (5 mL) and ether (10 mL) are then added to the mixture, and the organic layer is separated. The organic layer is washed with water, dried, and concentrated to give 3-bromomethyl-6-(2,6-diethyl-phenyl)-4-methoxy-pyridine-2-carbonitrile.

Workup

  1. customthe organic layer is separated
  2. washThe organic layer is washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6f58075feeb64cb9bc3a5b832fc04103
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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