Bromine → HCID 86668389, compound

HRID 529746Notes

Reaction equation

HRID 529746 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:18][CH3:19])=[C:8]([C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=1>O1CCOCC1>[Br:1][CH:11]([C:10]([C:8]1[CH:9]=[C:4]([Cl:3])[CH:5]=[CH:6][C:7]=1[O:18][CH3:19])=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 54012347Ethyl 3-(5-chloro-2-methoxyphenyl)-3-oxopropanoate

Product 1

HCID 86668389HCID 86668389, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Bromine (0.70 mL, 13.6 mmol) was added to a solution of ethyl 3-(5-chloro-2-methoxyphenyl)-3-oxopropanoate (3.39 g, 13.2 mmol) in dioxane (25 mL) and stirred for 1 hour. The reaction was poured onto ice water, extracted with ethyl acetate, the organics washed with water and brine and evaporated to dryness to give ethyl 2-bromo-3-(5-chloro-2-methoxyphenyl)-3-oxopropanoate. LCMS (method 1) [M+H]+=337.2, RT=3.84 min.

Workup

  1. additionThe reaction was poured onto ice water
  2. extractionextracted with ethyl acetate
  3. washthe organics washed with water and brine
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-539acebd4d4549e8b918e127997c0aaa
Source dataset
uspto-grants-2016_05
Patent number
US09346815B2

Reaction notes

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