Carbon tetrabromide → [(5-bromopentyl)-oxy]-N-butyl-N-methyl acetamide

HRID 1006749Notes

Reaction equation

HRID 1006749 reaction equation
Br[C:2]([Br:5])(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([N:29]([CH3:40])[C:30](=[O:39])[CH2:31][O:32][CH2:33][CH2:34][CH2:35][CH2:36]CO)[CH2:26][CH2:27][CH3:28]>C(Cl)Cl>[Br:5][CH2:2][CH2:36][CH2:35][CH2:34][CH2:33][O:32][CH2:31][C:30]([N:29]([CH2:25][CH2:26][CH2:27][CH3:28])[CH3:40])=[O:39]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 85613375HCID 85613375, compound

Product 1

HCID 54372321[(5-bromopentyl)-oxy]-N-butyl-N-methyl acetamideYield 81.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

13 g of tetrabromo-methane and 10.3 g of triphenyl-phosphine were added at −10° C. to a solution of 7.2 g of the product of Step C in 73 ml of methylene chloride. The reaction medium was stirred for one hour at 0° C. and chromatographed on silica (eluant: ethyl acetate—cyclohexane 7-3) to obtain 7.49 g of the desired compound.

Workup

  1. customchromatographed on silica (eluant: ethyl acetate—cyclohexane 7-3)

Sources & evidence

ORD record
ord-a00e8d9ef3b94d8692cb272af2bdb9d6
Source dataset
uspto-grants-2004_09
Patent number
US06790971B1

Reaction notes

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