Carbon tetrabromide → HCID 54394904, compound

HRID 584233Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][O:35][CH2:34][C@H:33]1[CH:38]=O)=[O:31])([CH3:28])([CH3:27])[CH3:26].C(=O)([O-])O.[Na+]>ClCCl>[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][O:35][CH2:34][C@H:33]1[CH:38]=[C:20]([Br:24])[Br:21])=[O:31])([CH3:28])([CH3:26])[CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

Triphenylphosphine (7.31 g) was added to a solution of carbon tetrabromide (4.62 g) in dichloromethane (15 ml) at 0° C. and the mixture was stirred at 0° C. for 15 minutes. A solution of (3S)-4-tert-butoxycarbonyl-3-formylmorpholine (1.5 g) in dichloromethane (15 ml) was added dropwise to the solution over 10 minutes at 0° C. and stirred for 3 hours, and the mixture was added saturated sodium hydrogen carbonate solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate three times. The combined organic layer was washed with brine, dried over magnesium sulfate, and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and n-hexane (4:6) to give (3R)-4-tert-butoxycarbonyl-3-(2,2-dibromoethenyl)morpholine as an oil.

Workup

stirringstirred for 3 hours
customThe organic layer was separated
extractionthe aqueous layer was extracted with ethyl acetate three times
washThe combined organic layer was washed with brine
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure
customThe residue was purified by column chromatography on silica gel using
additiona mixture of ethyl acetate and n-hexane (4:6)

Sources & evidence

ORD record: ord-a34b36a575984e14b7139396428f6dc5
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06924278B2

Reaction notes

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