Ethyl Bromide → Butyl ether

HRID 2218927Notes

Reaction equation

HRID 2218927 reaction equation
[Mg:1].[CH2:2]([O:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][CH2:4][CH3:5].Br[C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2.C([Br:24])C>>[CH2:2]([O:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][CH2:4][CH3:5].[C:12]12([Mg:1][Br:24])[CH2:21][CH:16]3[CH2:15][CH:14]([CH2:20][CH:18]([CH2:17]3)[CH2:19]1)[CH2:13]2

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 8909Butyl ether4×HCID 791061-BromoadamantaneHCID 5462224Magnesium

Product 2

HCID 8909Butyl etherHCID 178419608HCID 178419608, compound

Procedure

21.4 g (0.880 mol) of magnesium and 125.0 g (0.960 mol) of dibutyl ether were charged in a 1,000 ml flask equipped with a reflux condenser, a dropping funnel and a stirring apparatus, in an atmosphere of nitrogen, and after stirring was started, a solution having 172.1 g (0.800 mol) of 1-bromoadamantane and 4.36 g (0.0400 mol) of ethyl bromide diluted with 250.0 g (1.92 mol) of dibutyl ether was dropwise added thereto from the dropping funnel over a period of 2 hours under reflux of dibutyl ether, and then stirring was carried out for 4 hours under reflux of dibutyl ether, to obtain a dibutyl ether solution of 1-adamantyl magnesium bromide.

Workup

  1. customequipped with a reflux condenser, a dropping funnel
  2. additionwas dropwise added
  3. stirringstirring

Sources & evidence

ORD record
ord-e64ef9ff44794897b724df08f5602978
Source dataset
uspto-grants-2008_08
Patent number
US07413775B2

Reaction notes

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