2-Bromo-2-methylpropionyl bromide → HCID 18386553, compound

HRID 493413Notes

Reaction equation

HRID 493413 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][C:6]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)([CH3:22])[C:7]([C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)=[O:8].[Br:29][C:30]([CH3:35])([CH3:34])[C:31](Br)=[O:32]>ClCCl>[Br:29][C:30]([CH3:35])([CH3:34])[C:31]([C:19]1[CH:20]=[CH:21][C:16]([S:15][C:12]2[CH:13]=[CH:14][C:9]([C:7](=[O:8])[C:6]([CH3:5])([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[CH3:22])=[CH:10][CH:11]=2)=[CH:17][CH:18]=1)=[O:32]

Participants

5

Reactant 3

HCID 886852-Bromo-2-methylpropionyl bromideHCID 6451240Aluminum(III) ChlorideHCID 19879538HCID 19879538, compound

Product 1

HCID 18386553HCID 18386553, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.30 (32.20 mol) of AlCl3 were added in portion under stirring to a solution of 2.5 g (7.32 mmol) of 2-methyl-2-morpholin yl-1-(4-phenylsulphanyl-phenyl)-propan-1-one and 1.81 g (7.69 mmol) of α-bromoisobutyrylbromide (97.5% w/w) in 50 ml of dichloromethane, between 0 e 5° C. At the end of the addition the temperature was brought to 25° C. then, after 2.5 h, the reaction was quenched in 200 ml of iced water. The organic phase was separated and washed with water and 5% NaOH then dried with sodium sulphate, filtered and evaporated obtaining 3.59 g of product as a reddish oil.

Workup

  1. additionAt the end of the addition the temperature
  2. customwas brought to 25° C.
  3. customthe reaction was quenched in 200 ml of iced water
  4. customThe organic phase was separated
  5. washwashed with water and 5% NaOH
  6. dry with materialthen dried with sodium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-455f072b60f34eb6a36a8db146a9871d
Source dataset
uspto-grants-2009_05
Patent number
US07534880B2

Reaction notes

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