Bromine → 1-Bromo-6-chloro-3-hexanone

HRID 595241Notes

Reaction equation

HRID 595241 reaction equation
[Br:1]Br.[Cl:3][CH2:4][CH2:5][CH2:6][C:7]1([OH:10])[CH2:9][CH2:8]1>CC(O)C.O>[Br:1][CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5][CH2:4][Cl:3]

Participants

5

Reactant 2

HCID 24408BromineHCID 10953563HCID 10953563, compound

Product 1

HCID 152872301-Bromo-6-chloro-3-hexanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Bromine (2.0 mL, 39 mmol) was added slowly to a solution of 1-(3-chloro-propyl)-cyclopropanol (5.0 g, 34 mmol) in i-PrOH (80% in water, 30 mL) at 0° C. The reaction mixture was stirred at room temperature for 1 hr then diluted with water (15 mL). The aqueous layer was extracted with EtOAc (3×30 mL) and the organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford crude 1-bromo-6-chloro-hexan-3-one.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (3×30 mL)
  2. dry with materialthe organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-42724564a02e4f7488a32451dca1fa1f
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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