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

HRID 251595
Notes
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Reaction equation

HRID 251595 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent
HCID 3283Diethyl EtherSolvent
HCID 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-af4705fb5b824313a7bdcb6a153bf359
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07863454B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes