Bromine → HCID 68870510, compound

HRID 2105850Notes

Reaction equation

HRID 2105850 reaction equation
[Br:1]Br.[CH2:3]([O:5][C:6]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4]>C(O)(=O)C>[Br:1][C:15]1[C:14]([O:17][CH2:18][CH3:19])=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([O:5][CH2:3][CH3:4])[CH:16]=1

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 3530990Ethyl-2,5-diethoxybenzoate

Product 1

HCID 68870510HCID 68870510, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (0.338 mL, 6.60 mmol) in acetic acid (6 mL) was added dropwise to a mixture of ethyl 2,5-diethoxybenzoate (1.36 mL, 6.02 mmol) and acetic acid (24 mL) cooled in a water bath. After stirring 1 h, more bromine (0.102 mL, 1.99 mmol) was added dropwise to the reaction mixture. After stirring an additional 4 h, the reaction mixture was concentrated under reduced pressure and the residue was purified by flash column chromatography (eluting with 10% diethyl ether in hexanes) to give ethyl 4-bromo-2,5-diethoxybenzoate as an off-white solid (0.610 g, 32%).

Workup

  1. temperaturecooled in a water bath
  2. stirringAfter stirring an additional 4 h
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by flash column chromatography (eluting with 10% diethyl ether in hexanes)

Sources & evidence

ORD record
ord-d315a749e2874496a383174e3a3c4ec9
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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