Benzyl Bromide → 4-Benzyloxymethyl-2-methoxy-1-nitro-benzene

HRID 1821792Notes

Reaction equation

HRID 1821792 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[CH2:12][OH:13].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)C>[CH2:20]([O:13][CH2:12][C:11]1[CH:14]=[CH:15][C:16]([N+:17]([O-:19])=[O:18])=[C:9]([O:8][CH3:7])[CH:10]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 6029613-Methoxy-4-nitrobenzyl alcohol

Product 1

HCID 220463764-Benzyloxymethyl-2-methoxy-1-nitro-benzeneYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred suspension of finely powdered cesium carbonate (8.0 g, 24.5 mmol) was added 3-methoxy-4-nitrobenzyl alcohol (1.5 g, 8.18 mmol), followed by benzyl bromide, (2 mL, 16.4 mmol). After stirring at room temperature for 18 h, the suspension diluted with 100 mL diethyl ether, and washed with 3×50 mL water, then 50 mL brine. The organic phase was dried over MgSO4, filtered through a plug of silica, and concentrated. The resulting orange oil was purified by flash chromatography, eluting with 2:1 hexane-EtOAc, to give 1.87 g, (84%) of the benzyl ether. 1H NMR (400 MHz, CDCl3): δ 7.85 (d, J=8.2 Hz, 1H) 7.3-7.4 (m, 5H), 7.26 (s, 1H), 6.97 (d, J=8.2 Hz, 1H), 4.61 (s, 2H), 4.59 (s, 2H), 3.96 (s, 3H).

Workup

  1. washwashed with 3×50 mL water
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered through a plug of silica
  4. concentrationconcentrated
  5. customThe resulting orange oil was purified by flash chromatography
  6. washeluting with 2:1 hexane-EtOAc

Sources & evidence

ORD record
ord-5b9bd45166a2418e9362118064465109
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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