Bromine → HCID 11723190, compound

HRID 546274Notes

Reaction equation

HRID 546274 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2].[Br:18]Br>C(Cl)(Cl)Cl.[W]>[Br:18][CH:5]([C:6]1[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:4]([O:3][CH2:1][CH3:2])=[O:17]

Participants

5

Reactant 2

HCID 24408BromineHCID 10944431HCID 10944431, compound

Product 1

HCID 11723190HCID 11723190, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

A solution of ethyl 2-[2-(ethyloxy)-2-oxoethyl]benzoate (4.15 g, 17.5 mmol) in chloroform (70 ml) was treated with bromine (1.3 ml, 25 mmol) and stirred at reflux, whilst irradiating with a 120 W tungsten bulb, for 5 hrs. The mixture was cooled to 20° C., evaporated and purified by automated flash silica-gel column chromatography (using a Biotage SP4), eluting with 0-10% gradient of ethyl acetate in hexane (10 column volumes), to give ethyl 2-[1-bromo-2-(ethyloxy)-2-oxoethyl]benzoate (2.77 g) as a pale yellow oil.

Workup

  1. temperatureat reflux
  2. customevaporated
  3. custompurified by automated flash silica-gel column chromatography (
  4. washeluting with 0-10% gradient of ethyl acetate in hexane (10 column volumes)

Sources & evidence

ORD record
ord-d7d4128c3d9048e0987d805837c91250
Source dataset
uspto-grants-2011_05
Patent number
US07935832B2

Reaction notes

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