Bromine → alpha-Bromo-2'-methyl-4'-chloropropoxyacetophenone

HRID 8368

Reaction equation

HRID 8368 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][Cl:12])[CH:5]=[CH:4][C:3]=1[C:13](=[O:15])[CH3:14].[Br:16]Br.C(=O)(O)[O-].[Na+]>CCOCC>[Br:16][CH2:14][C:13]([C:3]1[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH2:10][CH2:11][Cl:12])=[CH:7][C:2]=1[CH3:1])=[O:15]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 693770792'-Methyl-4'-chloropropoxyacetophenone

Product 1

HCID 22015662alpha-Bromo-2'-methyl-4'-chloropropoxyacetophenone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of the product of Step A (9.33 g) in ether (42 mL) was treated with bromine (2.1 mL) and the mixture stirred for approximately 17 hours. The mixture was slowly poured into saturated sodium bicarbonate solution (100 mL) and then the organic layer was separated. The aqueous layer was washed with a fresh portion of ether (100 mL). The combined organic layers were washed with a fresh portion of water (100 mL), dried over magnesium sulfate, filtered and evaporated to give the title compound (11 g).

Workup

  1. customthe organic layer was separated
  2. washThe aqueous layer was washed with a fresh portion of ether (100 mL)
  3. washThe combined organic layers were washed with a fresh portion of water (100 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4527f79af08042b88d0e1d11f714554a
Source dataset
uspto-grants-2006_08
Patent number
US07087757B2

Linked notes

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