Carbon tetrabromide → 3-Methoxy-4-nitrobenzyl bromide

HRID 1830779Notes

Reaction equation

HRID 1830779 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>[CH3:13][O:12][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:8][Br:15]

Participants

5

Reactant 3

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

Product 1

HCID 126216043-Methoxy-4-nitrobenzyl bromideYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 250 mL round bottomed flask containing 10 g (54.6 mmol) of 4-nitro-3-methoxybenzyl alcohol in 30 mL THF was added, 36 g (109 mmol, 2 eq ) of carbon tetrabromide followed by 15.9 g (60 mmol, 1.1 eq.) triphenylphosphine at 0° C. The mixture was stirred at 0° C. for 3 hours. Upon removal of the solvent, the residue was purified by flash chromatography, eluting with 10:90 EtOAc-Hexane, to give 11 g (82%) of the product as a yellow solid. 1H NMR (400 MHz, CDCl3): δ7.86 (s, 1H), 7.84 (m, 1H), 7.12 (s, 1H), 7.07 (m, 1H), 4.47 (s, 2H), 4.00 (s, 3H).

Workup

  1. additionwas added
  2. customUpon removal of the solvent
  3. customthe residue was purified by flash chromatography
  4. washeluting with 10:90 EtOAc-Hexane

Sources & evidence

ORD record
ord-3d641405732b4ebebe5c8a1331f275f7
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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