Carbon tetrabromide → 3-Methoxy-4-nitrobenzyl bromide

HRID 2205893Notes

Reaction equation

HRID 2205893 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 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbon tetrabromide (0.543 g, 1.638 mmol) and triphenylphosphine (0.430 g, 1.638 mmol) were added to a solution of (3-methoxy-4-nitrophenyl)methanol (0.2 g, 1.092 mmol) in THF (5.46 mL). The reaction mixture was stirred at room temperature overnight before being concentrated under reduced pressure and purified via Biotage silica gel column chromatography eluting with (cyclohexane/EtOAc 99/1 to 80/20) to afford the title product as a yellow solid (220 mg, 82%). 1H NMR (500 MHz, CDCl3): δ 4.00 (s, 3H), 4.48 (s, 2H), 7.06 (dd, J=8.3, 1.7 Hz, 1H), 7.12 (d, J=1.7 Hz, 1H), 7.84 (d, J=8.3 Hz, 1H)

Workup

  1. concentrationbefore being concentrated under reduced pressure
  2. custompurified via Biotage silica gel column chromatography
  3. washeluting with (cyclohexane/EtOAc 99/1 to 80/20)

Sources & evidence

ORD record
ord-aa72bd05788545429b87bc0478e8e7b6
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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