Dimethylformamide → Ethyl 2,4-dibromo-3-(aminocarbonylmethoxy)benzoate

HRID 1835863Notes

Reaction equation

HRID 1835863 reaction equation
C([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[C:18]([OH:19])=[C:17]([Br:20])[CH:16]=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11].CN(C=O)C.Cl[CH2:27][C:28]([NH2:30])=[O:29]>O>[Br:7][C:8]1[C:18]([O:19][CH2:27][C:28]([NH2:30])=[O:29])=[C:17]([Br:20])[CH:16]=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 14851207Ethyl 2,4-dibromo-3-hydroxybenzoate

Product 1

HCID 12056854Ethyl 2,4-dibromo-3-(aminocarbonylmethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

0.853 g (6.20 mmol) of K2CO3, 0.154 g (0.90 mmol) of Kl and 1.000 g (3.10 mmol) of ethyl 2,4-dibromo-3-hydroxybenzoate were introduced into 15 ml of DMF. 0.346 g (3.70 mmol) of chloroacetamide was added at RT, and the mixture was heated for 6 hours at 120° C. The mixture was then poured into water and extracted with diisopropyl ether. The combined organic phases were washed with water, dried over Na2SO4 and concentrated completely. Drying in an oil-pump vacuum gave ethyl 2,4-dibromo-3-(aminocarbonylmethoxy)benzoate as a brown oil.

Workup

  1. extractionextracted with diisopropyl ether
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated completely
  5. customDrying in an oil-pump vacuum

Sources & evidence

ORD record
ord-4c05273c17f7454aa697309268dce4cd
Source dataset
uspto-grants-2004_08
Patent number
US06774086B2

Reaction notes

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