Ethyl Bromide → HCID 14371697, compound

HRID 2073601Notes

Reaction equation

HRID 2073601 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](/[C:11]2[CH:20]=[CH:19][C:18]3[C:17]([CH3:22])([CH3:21])[CH2:16][CH2:15][C:14]([CH3:24])([CH3:23])[C:13]=3[CH:12]=2)\[CH3:10])=[CH:4][CH:3]=1.[P:25]([O:32][CH2:33][CH3:34])([O:29]CC)[O:26][CH2:27][CH3:28].C(Br)C>[Ni](Br)Br>[CH3:21][C:17]1([CH3:22])[CH2:16][CH2:15][C:14]([CH3:23])([CH3:24])[C:13]2[CH:12]=[C:11](/[C:9](/[CH3:10])=[CH:8]/[C:5]3[CH:4]=[CH:3][C:2]([P:25]([O:26][CH2:27][CH3:28])(=[O:29])[O:32][CH2:33][CH3:34])=[CH:7][CH:6]=3)[CH:20]=[CH:19][C:18]1=2

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 31215Triethyl phosphiteHCID 14371696HCID 14371696, compound

Product 1

HCID 14371697HCID 14371697, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 278492Nickel(II) bromideCatalyst

Procedure

20 g (52 millimoles) of (E)-1-(4-bromophenyl)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propene and 0.86 g (7.5 mol %) of anhydrous nickel(II) bromide were heated to about 160° C. under nitrogen in a distillation apparatus equipped with a dropping funnel. 104 g (60 millimoles) of triethyl phosphite were then added dropwise in such a way that the rate of dropwise addition corresponded to the rate at which the ethyl bromide distilled off. Stirring was continued for 0.5 hour, after which the mixture was cooled, a little toluene was added and the mixture was evaporated down. The residue was filtered with ethyl acetate over silica gel. 14.2 g (62%) of the title compound of melting point 72.5°-73.5° C. (from heptane) were obtained in this manner. Preparation of 1-(bromophenyl)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propene

Workup

  1. customequipped with a dropping funnel
  2. additionthat the rate of dropwise addition
  3. distillationdistilled off
  4. temperatureafter which the mixture was cooled
  5. additiona little toluene was added
  6. customthe mixture was evaporated down
  7. filtrationThe residue was filtered with ethyl acetate over silica gel

Sources & evidence

ORD record
ord-e04e2cd162924802813ffcd6e103452b
Source dataset
uspto-grants-1990_04
Patent number
US04918212

Reaction notes

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