Ethanol → HCID 118093778, compound

HRID 1057005Notes

Reaction equation

HRID 1057005 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-])=O)[C:3]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)C>[Ni].O>[NH2:9][C:4]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[OH:8]

Participants

5

Reactant 2

HCID 702EthanolHCID 118093987HCID 118093987, compound

Product 1

HCID 118093778HCID 118093778, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

A solution of 4-bromo-2-nitro-3-phenoxyphenol (0.468 g, 1.51 mmol) in ethanol (11.2 mL, 192 mmol) was degassed with nitrogen and treated with a slurry of Raney Nickel 2800 in water (0.468 ml). The reaction mixture was degassed again with nitrogen and hydrogenated with a balloon of hydrogen for 30 min. The reaction suspension was diluted with dichloromethane and methanol and filtered through a pad of Celite. The pad of Celite was washed with ethyl acetate and dichloromethane and the filtrate was concentrated in vacuo to give brown oil. Purification by flash column chromatography (100% CH2Cl2 to 30% CH3CN/CH2Cl2 [CH3CN contained 5% MeOH]) gave the desired product (346 mg, 82%) as a tan solid. LCMS calculated for C12H11BrNO2 (M+H)+: m/z=280.0, 282.0. found: 280.0, 282.0.

Workup

  1. customThe reaction mixture was degassed again with nitrogen and hydrogenated with a balloon of hydrogen for 30 min
  2. additionThe reaction suspension was diluted with dichloromethane and methanol
  3. filtrationfiltered through a pad of Celite
  4. washThe pad of Celite was washed with ethyl acetate and dichloromethane
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto give brown oil
  7. customPurification by flash column chromatography (100% CH2Cl2 to 30% CH3CN/CH2Cl2 [CH3CN contained 5% MeOH])

Sources & evidence

ORD record
ord-f9b633bc95bd464db3e1b11f6223fdf4
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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