Bromine → HCID 68860671, compound

HRID 384600Notes

Reaction equation

HRID 384600 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5](=[O:28])[CH2:6][CH:7]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])=[CH:10][CH:9]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[CH3:3][O:4][C:5](=[O:28])[CH2:6][CH:7]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2([Br:1])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 68860933HCID 68860933, compound

Product 1

HCID 68860671HCID 68860671, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7.32 g (44.5 mmol) of bromine in 10 ml of methylene chloride is added dropwise at room temperature to a mixture of 10.18 g (37.10 mmol) of methyl3-phenyl-3-[4-(cyclohexylcarbonyl)phenyl]propionate in 250 ml of methylene chloride. The mixture is stirred for 16 hours at room temperature after which 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 8.19.0 g (62.5%) of methyl3-phenyl-3-[4-((1-bromocyclohexyl)carbonyl)phenyl]propionate. Mass spectrum: m/z 429.1 (M+H)+.

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-9e86ddf305e944a1a798ae88864c3cb5
Source dataset
uspto-grants-2013_02
Patent number
US08367743B2

Reaction notes

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