Carbon tetrabromide → HCID 22610214, compound

HRID 2306764Notes

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-52eeef5c144b4872b429cce8ab540f6f
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06828337B2

Reaction notes

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