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

HRID 8364

Reaction equation

HRID 8364 reaction equation
[F: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[F:1])=[O:15]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 69375838HCID 69375838, compound

Product 1

HCID 22015593alpha-Bromo-2'-fluoro-4'-chloropropoxyacetophenone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of the product of Step A (2.3 g) in ether (10 mL) was treated with bromine (0.51 mL) and the mixture stirred for approximately 17 hours. The mixture was slowly poured into saturated sodium bicarbonate solution (40 mL) and then the organic layer was separated. The aqueous layer was washed with a fresh portion of ether (40 mL). The combined organic layers were washed with a fresh portion of water (50 mL), dried over magnesium sulfate, filtered and evaporated to give the title compound (3.1 g).

Workup

  1. customthe organic layer was separated
  2. washThe aqueous layer was washed with a fresh portion of ether (40 mL)
  3. washThe combined organic layers were washed with a fresh portion of water (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-15da65bf675c4180b4c07eda81b5323b
Source dataset
uspto-grants-2006_08
Patent number
US07087757B2

Linked notes

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