Ethyl Bromide → HCID 12306485, compound

HRID 2121954Notes

Reaction equation

HRID 2121954 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH3:22].[NH4+].[Cl-]>CN(C=O)C>[CH2:21]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12])[CH3:22]

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 1387234-Hydroxy-3-Nitroacetophenone

Product 1

HCID 12306485HCID 12306485, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4′-hydroxy-3′-nitroacetophenone (1.0 g, 5.5 mmol) in anhydrous DMF (20 mL) was added anhydrous K2CO3 (3.0 g, 22 mmol) and then bromoethane (0.49 mL, 6.6 mmol). After heating at 80° C. for 20 h, the reaction mixture was cooled, combined with satd aqueous NH4Cl (50 mL) and extracted with Et2O (2×100 mL). The combined organic layers were washed with water (3×50 mL), 1 N NaOH (50 mL) and then brine (50 mL), dried (Na2SO4) and concentrated under reduced pressure to afford the title compound (1.1 g, 96%) as a light brown solid, which was used without further purification. 1H-NMR (CDCl3): δ 8.41 (1H, d), 8.15 (1H, dd), 7.14 (1H, d), 4.28 (2H, q), 2.61 (3H, s), 1.52 (3H, t).

Workup

  1. temperaturethe reaction mixture was cooled
  2. extractionextracted with Et2O (2×100 mL)
  3. washThe combined organic layers were washed with water (3×50 mL), 1 N NaOH (50 mL)
  4. dry with materialbrine (50 mL), dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-79710a7ed42d4d6ab165292bda2655d7
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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