Nitroethane → 1-(3-Bromophenyl)-3-nitrobutan-2-ol

HRID 517531Notes

Reaction equation

HRID 517531 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.C1CCN2C(=NCCC2)CC1.[N+:22]([CH2:25][CH3:26])([O-:24])=[O:23]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([OH:10])[CH:25]([N+:22]([O-:24])=[O:23])[CH3:26])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 20387554(3-Bromophenyl)acetaldehyde

Product 1

HCID 867114751-(3-Bromophenyl)-3-nitrobutan-2-olYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-bromophenyl)acetaldehyde (5.0 g, 0.025 mol) and DBU (7.6 mL, 0.05 mol) in THF (300 mL), Nitroethane (1.0 g, 0.03 mol) was added at 0° C. over 10 min. The reaction mixture was stirred for 3 h, quenched by the addition of H2O (50 mL) and extracted with EtOAc (100 mL×3). The combined organic layers were washed with H2O (2×30 mL) and brine (1×20 mL), dried over Na2SO4, filtered and concentrated to afford 1-(3-bromophenyl)-3-nitrobutan-2-ol (3.0 g, 44%) as a yellow oil. MS (ES+) C10H12BrNO3 requires: 273, 275 found: 274, 276 [M+2+H]+(1:1).

Workup

  1. customquenched by the addition of H2O (50 mL)
  2. extractionextracted with EtOAc (100 mL×3)
  3. washThe combined organic layers were washed with H2O (2×30 mL) and brine (1×20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4f83e53b36d44ea9a677a8e887eb197a
Source dataset
uspto-grants-2015_08
Patent number
US09115120B2

Reaction notes

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