1-Bromo-2,2-dimethylpropane → 4-(2,2-Dimethylpropyl)4-ethenylbenzene

HRID 1268922Notes

Reaction equation

HRID 1268922 reaction equation
[Mg].Br[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].Br[C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[CH2:14])=[CH:11][CH:10]=1>C(OCC)C.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Ni]Cl.[Fe]>[CH3:5][C:4]([CH3:7])([CH3:6])[CH2:3][C:12]1([CH:13]=[CH2:14])[CH:11]=[CH:10][CH:9]=[CH:16][CH2:15]1

Participants

6

Reactant 3

HCID 124151-Bromo-2,2-dimethylpropaneHCID 162634-BromostyreneHCID 5462224Magnesium

Product 1

HCID 866014194-(2,2-Dimethylpropyl)4-ethenylbenzeneYield 127.2%

Reagents, catalysts & solvents 2

HCID 178477753HCID 178477753, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 0.8 g (33.10 mmol) of magnesium turnings and 2.0 g (13.2 mmol) of 1-bromo-2,2-dimethylpropane in 10 mL diethyl ether was added a solution of 1.42 g (7.76 mmol) of 4-bromostyrene and 69 mg (0.13 mmol) of Ni(dppf)Cl2 The resulting reaction mixture was heated at refluc for 8 h. The reaction was quenched with 50% saturated NH4Cl, and was extracted with MTBE (2×150 mL). The combined extractions were washed with water, dried and concentrated. Flash chromatography on a Biotage 40M cartridge with hexanes as the eluant afforded 1.74 g of the title compound: 1H NMR (500 Mhz) δ 0.93 (s, 9H), 2.49 (s, 2H), 5.20 (d, J=10.9, 1H), 5.73 (d, J=17.6, 1H), 6.72 (dd, J1=17.6, J2=10.8, 1H), 7.10 (d, J=8.2, 2H), 7.33 (d, J=8.0, 2H); ESI-MS 161 (M+H); LC-1: 4.4 min.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated at refluc for 8 h
  3. customThe reaction was quenched with 50% saturated NH4Cl
  4. extractionwas extracted with MTBE (2×150 mL)
  5. extractionThe combined extractions
  6. washwere washed with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-574a8f6125484e9a83e8de25f36c594f
Source dataset
uspto-grants-2007_04
Patent number
US07199142B2

Reaction notes

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