Carbon tetrabromide → HCID 15895918, compound

HRID 2289621Notes

Reaction equation

HRID 2289621 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](=[O:15])[CH:4]=1.C(Br)(Br)(Br)[Br:17].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:17][CH2:2][C:3]1[CH:8]=[CH:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](=[O:15])[CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18698767HCID 18698767, compound

Product 1

HCID 15895918HCID 15895918, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Hydroxymethyl-1-phenyl-1H-pyridin-2-one from Step 4 (1.0 g, 5 mmol) was dissolved in CH2Cl2. CBr4 (6 mmol, 2 g) was added and the reaction mixture was cooled to 0°. PPh3 (6 mmol, 2.0 g) was added dropwise in CH2Cl2. The reaction mixture was stirred at 0° for 15 minutes and then warmed to room temperature. The reaction mixture was concentrated and purified on a column of silica eluting with (30% EtOAc/hexane to 50% EtOAc/hexane) to give 4-bromomethyl-1-phenyl-1H-pyridin-2-one (8, x=H) as a white solid.

Workup

  1. temperaturethe reaction mixture was cooled to 0°
  2. concentrationThe reaction mixture was concentrated
  3. custompurified on a column of silica eluting with (30% EtOAc/hexane to 50% EtOAc/hexane)

Sources & evidence

ORD record
ord-6d718b4645534d709ba223c9da18296c
Source dataset
uspto-grants-2000_07
Patent number
US06093737

Reaction notes

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