Bromine → HCID 20084345, compound

HRID 327556Notes

Reaction equation

HRID 327556 reaction equation
[CH3:1][C:2]([CH:4]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=[O:3].[Br:12]Br>CO>[CH:4]1([C:2]([CH2:1][Br:12])=[O:3])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 24408BromineHCID 12757496HCID 12757496, compound

Product 1

HCID 20084345HCID 20084345, compoundYield 217.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An ice cold solution of 5.5 g of cyclooctyl methyl ketone in 50 ml of methyl alcohol was treated dropwise with 1.95 g of bromine. After 5 min, the ice bath was removed and the reaction mixture was allowed to warm to room temperature. The reaction mixture was then diluted with 200 ml of water and extracted with ethyl ether (3×60 ml). The combined extracts were washed with saturated sodium bicarbonate, brine, dried (MgSO4) and condensed in vacuo to yield 6.2 g of bromomethyl cyclooctyl ketone as an oil.

Workup

  1. customthe ice bath was removed
  2. additionThe reaction mixture was then diluted with 200 ml of water
  3. extractionextracted with ethyl ether (3×60 ml)
  4. washThe combined extracts were washed with saturated sodium bicarbonate, brine
  5. customdried
  6. custom(MgSO4) and condensed in vacuo

Sources & evidence

ORD record
ord-3b60817d8db0465a99cc71d35dc27e7f
Source dataset
uspto-grants-1993_12
Patent number
US05273986

Reaction notes

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