Carbon tetrabromide → HCID 20638389, compound

HRID 1858996Notes

Reaction equation

[Br:1][C:2]([Br:5])(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:25]([Si:29]([CH3:46])([CH3:45])[O:30][C@H:31]1[CH2:39][CH2:38][CH2:37][C@@:36]2([CH3:40])[C@H:32]1[CH2:33][CH2:34][C@@H:35]2[C@H:41]([CH3:44])[CH:42]=O)([CH3:28])([CH3:27])[CH3:26]>ClCCl>[C:25]([Si:29]([CH3:46])([CH3:45])[O:30][C@H:31]1[CH2:39][CH2:38][CH2:37][C@@:36]2([CH3:40])[C@H:32]1[CH2:33][CH2:34][C@@H:35]2[C@H:41]([CH3:42])[CH:44]=[C:2]([Br:5])[Br:1])([CH3:27])([CH3:28])[CH3:26]

Participants

Conditions

Temperature: -20 °C

Procedure

Typically, tetrabromomethane (16.8 g; 50.6 mmol) is dissolved in dichloromethane (80 ml). Triphenylphosphine (26.5 g; 101.1 mmol) in solution in dichloromethane (40 ml) is added dropwise. The reaction mixture is cooled to -20° C. and the compound (S)-2-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-propan-1-al (J. Org Chem: 1992, 57, 3173 ) in solution in dichloromethane (30 ml) is added dropwise. The reaction mixture is allowed to reach room temperature and is then poured on ice. The mixture is extracted twice with ethyl-acetate (250 ml); the organic phase is washed twice with brine (100 ml), dried over sodium sulfate. After evaporation of the solvents and flash-chromatography over silica gel (hexanes/ethyl acetate 98:2) the compound (1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-1-[(S)-3,3-dibromo-1-methyl-allyl]-7a-methyl-octahydro-indene (8.94 g; Yield 81%) was obtained as a colorless oil.

Workup

customto reach room temperature
additionis then poured on ice
extractionThe mixture is extracted twice with ethyl-acetate (250 ml)
washthe organic phase is washed twice with brine (100 ml)
dry with materialdried over sodium sulfate

Sources & evidence

ORD record: ord-91f491e2d0f44fec9e1a854f2ec6684d
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06153605

Reaction notes

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