Water → Ethyl 2,4-dibromo-3-(ethylcarbonylmethoxy)benzoate

HRID 585325Notes

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].Br[CH2:22][C:23](=[O:26])[CH2:24][CH3:25].O>CN(C=O)C>[Br:7][C:8]1[C:18]([O:19][CH2:22][C:23]([CH2:24][CH3:25])=[O:26])=[C:17]([Br:20])[CH:16]=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

0.853 g (6.20 mmol) of K2CO3, 0.154 g (0.90 mmol) of KI and 1.000 g (3.10 mmol) of ethyl 2,4-dibromo-3-hydroxybenzoate were initially charged in 10 ml of DMF. At RT, 0.621 g (3.70 mmol) of 1-bromo-2-butanone was added, and the mixture was then heated at 80° C. for 4 h. The mixture was then poured into water and extracted with diisopropyl 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-(ethylcarbonylmethoxy)benzoate as a brown oil.

Workup

extractionextracted with diisopropyl ether
washThe combined organic phases were washed with water
dry with materialdried over Na2SO4
customevaporated to dryness
customDrying under oil pump vacuum

Sources & evidence

ORD record: ord-0d5c6681367a462bbbad58a5349721f0
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06930208B2

Reaction notes

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