Carbon tetrabromide → 6-(3-Bromomethyl-pent-2-enyl)-5-ethyl-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one

HRID 33672Notes

Reaction equation

HRID 33672 reaction equation
[CH2:1]([C:3]1[C:4]([CH3:27])=[C:5]2[C:9](=[C:10]([O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:11]=1[CH2:12][CH:13]=[C:14]([CH2:17]O)[CH2:15][CH3:16])[C:8](=[O:26])[O:7][CH2:6]2)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:48]>C(Cl)Cl>[Br:48][CH2:17][C:14]([CH2:15][CH3:16])=[CH:13][CH2:12][C:11]1[C:10]([O:19][CH2:20][CH2:21][Si:22]([CH3:23])([CH3:25])[CH3:24])=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[O:26])=[C:4]([CH3:27])[C:3]=1[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 670102685-Ethyl-6-(3-hydroxymethyl-pent-2-enyl)4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one

Product 1

HCID 670103606-(3-Bromomethyl-pent-2-enyl)-5-ethyl-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-oneYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Ethyl-6-(3-hydroxymethyl-pent-2-enyl)-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one (35.4 mg, 0.090 mmol) was dissolved in DCM (3.0 mL). Polymer-bound triphenylphosphine (3 mmol/g, 90.7 mg) was added and the mixture was mechanically stirred at room temperature. Carbon tetrabromide (90.2 mg, 0.272 mmol) was added and the solution was stirred at room temperature. After 2 hrs, the reaction was filtered and the solvent was removed in vacuo. The crude material was purified by silica gel chromatography to provide 32.0 mg (78%) of the desired product. The material was used in the next step without further characterization.

Workup

  1. stirringthe solution was stirred at room temperature
  2. filtrationthe reaction was filtered
  3. customthe solvent was removed in vacuo
  4. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7f33c81f3fa64345b63084c5f18daaab
Source dataset
uspto-grants-2008_09
Patent number
US07429565B2

Reaction notes

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