Chloroacetone → Ethyl 2,4-dibromo-3-(2-ethoxyiminopropyloxy)benzoate

HRID 585328Notes

Reaction equation

HRID 585328 reaction equation
[Br:1][C:2]1[C:12]([O:13][CH2:14][C:15]([CH3:17])=O)=[C:11]([Br:18])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].BrC1C(O)=C(Br)C=CC=1C(OCC)=O.ClCC(=O)C.C([O-])([O-])=O.[Na+].[Na+].Cl.[CH2:45]([O:47][NH2:48])[CH3:46]>CO.O>[Br:1][C:2]1[C:12]([O:13][CH2:14][C:15](=[N:48][O:47][CH2:45][CH3:46])[CH3:17])=[C:11]([Br:18])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

8

Reactant 5

HCID 6571ChloroacetoneHCID 10340Sodium CarbonateHCID 76850O-ethylhydroxylamine hydrochlorideHCID 14851207Ethyl 2,4-dibromo-3-hydroxybenzoateHCID 22340636Ethyl 2,4-dibromo-3-(methylcarbonylmethoxy)benzoate

Product 1

HCID 85873781Ethyl 2,4-dibromo-3-(2-ethoxyiminopropyloxy)benzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

1.00 g (2.60 mmol) of ethyl 2,4-dibromo-3-(methylcarbonylmethoxy)benzoate (prepared from ethyl 2,4-dibromo-3-hydroxybenzoate and chloroacetone analogously to preparation a), step 1, above) and 0.614 g (5.80 mmol) of Na2CO3 were initially charged in 10 ml of methanol. 0.529 g (5.30 mmol) of O-ethyl hydroxylamine hydrochloride, dissolved in 12 ml of water, was added dropwise and the mixture was stirred at RT for 2 h. The mixture was then poured into water and extracted with diethyl ether. The combined organic phases were washed with water, dried over Na2SO4 and evaporated to dryness. Drying under oil pump vacuum gave ethyl 2,4-dibromo-3-(2-ethoxyiminopropyloxy)benzoate as a brown oil.

Workup

  1. additionwas added dropwise
  2. extractionextracted with diethyl ether
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customDrying under oil pump vacuum

Sources & evidence

ORD record
ord-5eb0da5038484969a784c2cfbcbb1d8a
Source dataset
uspto-grants-2005_08
Patent number
US06930208B2

Reaction notes

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