Pyridine → HCID 19743036, compound

HRID 254481Notes

Reaction equation

HRID 254481 reaction equation
P(Br)(Br)[Br:2].[C:5]1([CH3:15])[CH:10]=[CH:9][C:8]([CH:11](O)[CH2:12][CH3:13])=[CH:7][CH:6]=1.N1C=CC=CC=1>C(OCC)C>[Br:2][CH:11]([C:8]1[CH:9]=[CH:10][C:5]([CH3:15])=[CH:6][CH:7]=1)[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 27938731-(4-Methylphenyl)-1-propanol

Product 1

HCID 19743036HCID 19743036, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4.5 g (1.6 ml, 16.7 mmol) Phosphorus tribromide were added portion-wise, with stirring to a solution of 4.98 g (33.0 mmol) rac-1-p-tolyl-propan-1-ol and 0.37 ml pyridine in 17 ml anhydrous diethyl ether at 0° C. The reaction mixture was warmed to ambient temperature and the reaction monitored by HPLC to completion. The reaction mixture was poured onto ice-water and the whole was extracted with dichloromethane. The organic phase was washed with brine, dried over MgSO4 and evaporated to give rac-1-(1-bromo-propyl)-4-methyl-benzene as a colourless oil that did not require further purification: NMR (CDCl3, ppm): 1.01 (3H, t), 2.28 (2H, m), 2.40 (3H, s), 4.92 (1H, t), 7.20 (4H, m).

Workup

  1. additionThe reaction mixture was poured onto ice-water
  2. extractionthe whole was extracted with dichloromethane
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-eaafc2a8cffb4ce7ac4023c8d4619049
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

Loading…