Carbon tetrabromide → tert-butyl N-(3-bromopropyl)carbamate

HRID 973748Notes

Reaction equation

HRID 973748 reaction equation
[C:1]([Br:5])(Br)(Br)Br.[C:6]([O:10][C:11]([NH:13][CH2:14][CH2:15]CO)=[O:12])([CH3:9])([CH3:8])[CH3:7]>C(#N)C.O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:6]([O:10][C:11]([NH:13][CH2:14][CH2:15][CH2:1][Br:5])=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 2

HCID 11205Carbon tetrabromideHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 4460490tert-butyl N-(3-bromopropyl)carbamateYield 76.9%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 11776TriphenylphosphineSolvent

Procedure

25 g of carbon tetrabromide in solution in 50 ml of acetonitrile were slowly added at a temperature between 20° and 25° C. to a solution of 9 g of the product of Step A in 120 ml of tetrahydrofuran and 19.7 g of triphenyl phosphine. After stirring for 15 hours, the insoluble part was filtered off and the filtrate was concentrated to dryness under reduced pressure. The 45 g of residue were chromatographed on silica (eluant: hexane-ethyl acetate (8-2)) to obtain 9.4 g of the expected product melting at 40° C.

Workup

  1. filtrationthe insoluble part was filtered off
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure
  3. customThe 45 g of residue were chromatographed on silica (eluant: hexane-ethyl acetate (8-2))

Sources & evidence

ORD record
ord-1a86c62c9b3c4118a778256073a3bded
Source dataset
uspto-grants-1991_11
Patent number
US05064861

Reaction notes

Loading…