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

HRID 33007Notes

Reaction equation

HRID 33007 reaction equation
[CH2:1]([C:3]1[C:4]([CH3:26])=[C:5]2[C:9](=[C:10]([O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:11]=1[CH2:12][CH:13]=[C:14]([CH3:17])[CH2:15]O)[C:8](=[O:25])[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:47]>C(Cl)Cl>[Br:47][CH2:15][C:14]([CH3:17])=[CH:13][CH2:12][C:11]1[C:10]([O:18][CH2:19][CH2:20][Si:21]([CH3:23])([CH3:24])[CH3:22])=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[O:25])=[C:4]([CH3:26])[C:3]=1[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 670098805-Ethyl-6-(4-hydroxy-3-methyl-but-2-enyl)4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one

Product 1

HCID 670113116-(4-Bromo-3-methyl-but-2-enyl)-5-ethyl-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-oneYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Ethyl-6-(4-hydroxy-3-methyl-but-2-enyl)-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one (57.2 mg, 0.152 mmol) was dissolved in DCM (3.5 mL). Polymer-bound triphenylphosphine (3 mmol/g, 152.1 mg) was added and the mixture was mechanically stirred at room temperature. Carbon tetrabromide (151.3 mg, 0.456 mmol) was added and the solution was stirred at room temperature. After 2 hours, the reaction was filtered and the solvent was removed in vacuo. The crude material was purified by silica gel chromatography to provide 58.0 mg (87%) of the desired product. 1H NMR (300 MHz, CDCl3): δ=0.04 (s, 9H), 1.15 (t, J=7.8 Hz, 3H), 1.25 (m, 2H), 1.95 (s, 3H), 2.20 (s, 3H), 2.70 (q, J=7.8 Hz, 2H), 3.52 (d, J=6.3 Hz, 2H), 3.94 (s, 2H), 4.28 (m, 2H), 5.14 (s, 2H), 5.50 (m, 1H) ppm.

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-96e94ff5dd2c4528be3533d9f34309fe
Source dataset
uspto-grants-2008_09
Patent number
US07427636B2

Reaction notes

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