Carbon tetrabromide → 3-Methoxy-4-nitrobenzyl bromide

HRID 2205914Notes

Reaction equation

HRID 2205914 reaction equation
[C:1]([Br:5])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:25][O:26][C:27]1[CH:28]=[C:29](CO)[CH:30]=[CH:31][C:32]=1[N+:33]([O-:35])=[O:34]>C1COCC1>[Br:5][CH2:1][C:29]1[CH:30]=[CH:31][C:32]([N+:33]([O-:35])=[O:34])=[C:27]([O:26][CH3:25])[CH:28]=1

Participants

5

Reactant 3

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

Product 1

HCID 126216043-Methoxy-4-nitrobenzyl bromideYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbon tetrabromide (1.63 g, 4.9 mmol) and triphenylphosphine (1.29 g, 4.9 mmol) were added to a solution of (3-methoxy-4-nitrophenyl)methanol (0.6 g, 3.3 mmol) in THF (15 mL). The reaction mixture was stirred at room temperature for 24 hours before being concentrated under reduced pressure and purified on silica gel column chromatography eluting with 20% ethyl acetate in hexane to afford the title compound (0.67 g, 95%). 1H-NMR (500 MHz, CDCl3): δ 4.00 (s, 3H), 4.48 (s, 2H), 7.04 (dd, J=8.3 Hz, 1.7 Hz, 1H), 7.12 (d, J=1.7 Hz, 1H), 7.83 (d, J=8.3 Hz, 1H).

Workup

  1. concentrationbefore being concentrated under reduced pressure
  2. custompurified on silica gel column chromatography
  3. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-deda73c084914bcb92cb008de37262a9
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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