Bromine → HCID 90185211, compound

HRID 2167689Notes

Reaction equation

HRID 2167689 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[Br:15]Br>C(Cl)(Cl)Cl>[Br:15][CH:9]([C:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)=[O:14])[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 735885Methyl (4-chlorobenzoyl)acetate

Product 1

HCID 90185211HCID 90185211, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

To a chloroform (20 mL) solution of methyl 3-(4-chlorophenyl)-3-oxopropanoate (1.0 g), bromine (0.12 mL) was added, and the resultant was stirred at 70° C. for 1 hour under sealed conditions. Then, bromine (0.12 mL) was further added thereto, and the resultant was further stirred at 70° C. for 1 hour under sealed conditions. The reaction solution was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=100/0→75/25) to obtain the title compound (0.44 g) as a pale yellow oil.

Workup

  1. stirringthe resultant was further stirred at 70° C. for 1 hour under sealed conditions
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=100/0→75/25)

Sources & evidence

ORD record
ord-8d6f112072f24cf4bc14257a112581f7
Source dataset
uspto-grants-2015_06
Patent number
US09045466B2

Reaction notes

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