Ethyl Bromide → Butyl ether

HRID 2218928Notes

Reaction equation

HRID 2218928 reaction equation
[Mg:1].Br[C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.C([Br:15])C.[CH2:16]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19]>>[CH2:16]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19].[C:3]12([Mg:1][Br:15])[CH2:12][CH:7]3[CH2:6][CH:5]([CH2:11][CH:9]([CH2:8]3)[CH2:10]1)[CH2:4]2

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 8909Butyl ether2×HCID 791061-BromoadamantaneHCID 5462224Magnesium

Product 2

HCID 8909Butyl etherHCID 178419608HCID 178419608, compound

Procedure

2.92 g (0.120 mol) of magnesium and 30 ml of dibutyl ether were charged in a 200 ml Schlenk tube equipped with a reflux condenser, a dropping funnel and a stirring apparatus in an atmosphere of nitrogen, and a solution having 21.5 g (0.100 mol) of 1-bromoadamantane and 1.09 g (0.0100 mol) of ethyl bromide dissolved in 40 ml of dibutyl ether was dropwise added thereto from the dropping funnel at 80° C. over a period of 1 hour, and stirring was carried out further for 2 hours at 120° C. 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. waitwas carried out further for 2 hours at 120° C.

Sources & evidence

ORD record
ord-5a7e2e2d0712406eb4dd39a78a10cde8
Source dataset
uspto-grants-2008_08
Patent number
US07413775B2

Reaction notes

Loading…