Carbon tetrabromide → Methyl 4-(1-bromobutyl)benzoate

HRID 2190888Notes

Reaction equation

HRID 2190888 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O[CH:21]([C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1)[CH2:22][CH2:23][CH3:24].C(Br)(Br)(Br)[Br:36]>C(Cl)Cl>[Br:36][CH:21]([C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1)[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 10443031HCID 10443031, compound

Product 1

HCID 22399772Methyl 4-(1-bromobutyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of PPh3 (42.2 g. 320 mmol) in DCM (200 mL) was added dropwise to a solution of methyl 4-(1-hydroxybutyl)benzoate (33.5 g, 160 mmol) and CBr4 (53.1 g, 320 mmol) in DCM (1200 mL) at 0° C. Once the addition was complete, the mixture was allowed to warm to room temperature and was stirred overnight. The mixture was concentrated, then the resulting residue was purified by silica gel chromatography eluting with 5% EtOAc/petroleum ether to afford the title compound. 1H NMR (300 MHz, CDCl3) δ 8.00 (d, J=6 Hz, 2 H); 7.45 (d, J=6 Hz, 2 H); 4.95 (t, J=7 Hz, 1 H); 3.91 (s, 3 H); 2.19-2.32 (m, 1 H); 2.02-2.14 (m, 1 H); 1.43-1.55 (m, 1 H); 1.24-1.38 (m, 1 H); 0.93 (t, J=7 Hz, 3 H).

Workup

  1. additionOnce the addition
  2. concentrationThe mixture was concentrated
  3. customthe resulting residue was purified by silica gel chromatography
  4. washeluting with 5% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-49900ef6fd51451e9fdf4f293a81a221
Source dataset
uspto-grants-2012_12
Patent number
US08324384B2

Reaction notes

Loading…