Benzyl Bromide → 1-Tert-butyl-2-(benzyloxy)-5-bromo-4-nitrobenzene

HRID 74000Notes

Reaction equation

HRID 74000 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([Br:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.O>[C:1]([C:5]1[CH:10]=[C:9]([Br:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:6]=1[O:15][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 574702362-Tert-butyl-4-bromo-5-nitrophenol

Product 1

HCID 574702371-Tert-butyl-2-(benzyloxy)-5-bromo-4-nitrobenzeneYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-tert-butyl-4-bromo-5-nitrophenol (C-14-a) (1.1 g, 4 mmol) and Cs2CO3 (1.56 g, 4.8 mmol) in DMF (8 mL) was added benzyl bromide (500 μL, 4.2 mmol). The mixture was stirred at room temperature for 4 h, diluted with H2O and extracted twice with EtOAc. The combined organic layers were washed with brine and dried over MgSO4. After removal of solvent, the residue was purified by column chloromatography (0-5% EtOAc-Hexane) to yield 1-tert-butyl-2-(benzyloxy)-5-bromo-4-nitrobenzene (1.37 g, 94%). 1H NMR (400 MHz, CDCl3) 7.62 (s, 1H), 7.53 (s, 1H), 7.43 (m, 5H), 5.22 (s, 2H), 1.42 (s, 9H).

Workup

  1. extractionextracted twice with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. customAfter removal of solvent
  5. customthe residue was purified by column chloromatography (0-5% EtOAc-Hexane)

Sources & evidence

ORD record
ord-372ad04aedf5491c98161c14d895b53e
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

Loading…