Carbon tetrabromide → 3-Methoxy-4-nitrobenzyl bromide

HRID 1019751Notes

Reaction equation

HRID 1019751 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]O)=[CH:6][C:5]=1[O:12][CH3:13])([O-:3])=[O:2].C(Br)(Br)(Br)[Br:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:15][CH2:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([O:12][CH3:13])[CH:6]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 6029613-Methoxy-4-nitrobenzyl alcohol

Product 1

HCID 126216043-Methoxy-4-nitrobenzyl bromideYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-nitro-3-methoxybenzyl alcohol (1.0 g, 5.46 mmol) in THF (5 ml) was cooled to 0° C. and carbon tetrabromide (3.62 g, 10.92 mmol) and triphenylphosphine (1.57 g, 6.00 mmol) were added. The reaction mixture was stirred at 0° C. for 2 hours then the solvents were removed under reduced pressure. The residue was purified by column chromatography on neutral silica gel using 5-8% EtOAc in hexane to give the title compound (1.25 g, 93%).

Workup

  1. customthe solvents were removed under reduced pressure
  2. customThe residue was purified by column chromatography on neutral silica gel using 5-8% EtOAc in hexane

Sources & evidence

ORD record
ord-c08c01feb48a4846b3ac3ef296680dcd
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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