2-Bromopropane → 5-Benzyloxy-2-isopropoxynitrobenzene

HRID 1420856Notes

Reaction equation

HRID 1420856 reaction equation
Br[CH:2]([CH3:4])[CH3:3].[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:2]([CH3:4])[CH3:3])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 46066344-(Benzyloxy)-2-nitrophenol

Product 1

HCID 187826055-Benzyloxy-2-isopropoxynitrobenzeneYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-Bromopropane (4.51 mL, 5.90 g, 48 mmol) was added to a mixture of 4-benzyloxy-2-nitrophenol (J.Biol.Chem., 1985, 260, 3440, 2.94 g, 12 mmol) and potassium carbonate (9.95 g, 72 mmol) in dimethylformamide (20 mL) and the mixture was stirred at 50° C. for 22 h. The mixture was cooled, diluted with water (100 mL) and extracted with ethyl acetate (3×100 mL). The combined organic fractions were washed with aqueous sodium hydroxide (1M, 4×100 mL) and brine (100 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as an orange oil (3.40 g, 99%). 1H NMR (360 MHz, CDCl3) δ 7.41-7.33 (6H, m), 7.12 (1H, dd, J 9.1, 3.1 Hz), 7.02 (1H, d, J 9.1 Hz), 5.05 (2H, s), 4.52 (1H, hept, J 6.1 Hz), and 1.35 (6H, d, J 6.1 Hz).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organic fractions were washed with aqueous sodium hydroxide (1M, 4×100 mL) and brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-57bf91a6b0cb4e08b0aac83d573304ba
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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