1-Bromo-2-butanone → HCID 135974501, compound

HRID 734411Notes

Reaction equation

HRID 734411 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].O1CCOCC1.Br[CH2:20][C:21](=O)[CH2:22][CH3:23]>C1(C)C=CC=CC=1>[CH2:22]([C:21]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([OH:1])=[C:3]([O:11][CH3:12])[CH:4]=2)[O:7][CH:20]=1)[CH3:23]

Participants

5

Reactant 3

HCID 131561-Bromo-2-butanoneHCID 312751,4-DioxaneHCID 354088Vanillamide

Product 1

HCID 135974501HCID 135974501, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-hydroxy-3-methoxybenzamide (460 mg, 2.75 mmol) (Example 38) in toluene (3 mL)/1,4-dioxane (3 mL), was added 1-bromo-2-butanone (623.29 mg, 4.13 mmol). The solution was heated to reflux for 18 h. The reaction mixture was cooled to rt, and the solvent was removed under reduced pressure. The crude residue was purified on silica gel to give the title compound as a yellow oil (434 mg, 72%). 1H NMR (400 MHz, DMSO-d6) δ 9.60 (s, 1H), 7.78 (s, 1H), 7.39 (d, 1H), 7.36 (dd, 1H), 6.83 (d, 1H), 3.79 (s, 3H), 2.45 (m, 2H), 1.18 (t, 3H).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 18 h
  3. customthe solvent was removed under reduced pressure
  4. customThe crude residue was purified on silica gel

Sources & evidence

ORD record
ord-b26dfe7190dc442aab5f4c70fb84c822
Source dataset
uspto-grants-2009_09
Patent number
US07592361B2

Reaction notes

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