Carbon tetrabromide → 2-(2-Bromoethyl)-6,6-dimethylbicyclo(3.1.1)hept-2-ene

HRID 710350Notes

Reaction equation

HRID 710350 reaction equation
[CH3:1][C:2]1([CH3:12])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH:5]=[C:6]2[CH2:9][CH2:10]O.C(Br)(Br)(Br)[Br:14].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:14][CH2:10][CH2:9][C:6]1[CH:7]2[CH2:8][CH:3]([CH2:4][CH:5]=1)[C:2]2([CH3:12])[CH3:1]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 31408Nopol

Product 1

HCID 202771482-(2-Bromoethyl)-6,6-dimethylbicyclo(3.1.1)hept-2-eneYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethanol (0.835 g, 4.87 mmol), CBr4 (1.83 g, 5.5 mmol) and PPh3 (1.44 g, 5.5 mmol) in anhydrous CH2Cl2 (10 ml) was stirred for 2 h at room temperature. The solvent was evaporated to dryness and the residue was treated with EtOAc (10 ml) and filtered through a SiO2 bead to give the title compound (1.03 g; 90%), as colourless oil. 1H-NMR (CDCl3) 0.82 (s, 3H); 1.26 (s, 3H); 1.99-2.37 (m, 6H); 2.5 (tr, 2H, J=7.88 Hz); 3.34 (tr, 2H, J=7.27 Hz); 5.31 (broad s, 1H).

Workup

  1. customThe solvent was evaporated to dryness
  2. additionthe residue was treated with EtOAc (10 ml)
  3. filtrationfiltered through a SiO2 bead

Sources & evidence

ORD record
ord-ce0d2fcc4eed476ebf4d61dddefe8af4
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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