Bromine → HCID 68861696, compound

HRID 384596Notes

Reaction equation

HRID 384596 reaction equation
[Br:1]Br.[CH3:3][CH:4]([CH3:25])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1)=[O:6].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:4]([CH3:25])([CH3:3])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 68861022HCID 68861022, compound

Product 1

HCID 68861696HCID 68861696, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 29.4 g (0.184 mol) of bromine in 50 ml of methylene chloride is added drop wise at room temperature to a mixture of 52.0 g (0.168 mol) of methyl 3-[4-(2-methylpropionyl)phenyl]-3-phenylpropanoate in 250 ml of methylene chloride. A small exotherm is controlled using a water bath. The mixture is stirred for 16 hours at room temperature. The reaction mixture is poured into a 5% aqueous sodium thiosulfate solution and stirred for 10 minutes. The organic layer is washed twice with 5% aqueous sodium thiosulfate solution, once with 10% sodium bicarbonate solution, dried over sodium sulfate, and concentrated to give 64.0 grams (98% yield) of methyl 3-[4-(2-bromo-2-methylpropionyl)phenyl]-3-phenylpropanoate.

Workup

  1. stirringstirred for 10 minutes
  2. washThe organic layer is washed twice with 5% aqueous sodium thiosulfate solution, once with 10% sodium bicarbonate solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2e5c829612794c56afa6ad637ce4580f
Source dataset
uspto-grants-2013_02
Patent number
US08367743B2

Reaction notes

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