Carbon tetrabromide → HCID 22610214, compound

HRID 1860303Notes

Reaction equation

[C:1]([Br:5])(Br)(Br)[Br:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:25][C:26]1([CH3:44])[CH2:34][CH2:33][C:32]([CH3:36])([CH3:35])[C:31]2[CH2:30][C:29]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])([CH:37]=O)[CH2:28][C:27]1=2.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:2][C:1]([Br:5])=[CH:37][C:29]1([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:28][C:27]2[C:26]([CH3:25])([CH3:44])[CH2:34][CH2:33][C:32]([CH3:36])([CH3:35])[C:31]=2[CH2:30]1

Participants

Conditions

Temperature: 0 °C

Procedure

4.9 g of carbon tetrabromide were dissolved in 75 ml of methylene chloride and treated dropwise with a solution of 7.7 g of triphenylphosphine in 80 ml of methylene chloride at a temperature of −20° C. The slightly orange solution was stirred at 0° C. for 15 minutes, then treated with a solution of 2 g of 4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-indene-2-carbaldehyde in 20 ml of methylene chloride. The reaction mixture was stirred at room temperature for 2 hours, then poured on ice/water and diluted aqueous sodium bicarbonate solution and extracted with methylene chloride. The yellow oil which was received after drying of the organic phase and evaporation of the solvent, was further purified with flash chromatography (silica gel, hexane/ethyl acetate=20:1) to give 2-(2,2-dibromo-vinyl)-4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-indene as a slightly yellow oil.

Workup

stirringThe reaction mixture was stirred at room temperature for 2 hours
extractionextracted with methylene chloride
customafter drying of the organic phase and evaporation of the solvent
customwas further purified with flash chromatography (silica gel, hexane/ethyl acetate=20:1)

Sources & evidence

ORD record: ord-838431be02e148148d456c408863f4fb
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528677B1

Reaction notes

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