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

HRID 474235Notes

Reaction equation

HRID 474235 reaction equation
O[CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:33]>ClCCl>[Br:33][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 4460490tert-butyl N-(3-bromopropyl)carbamateYield 66.46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-hydroxypropylcarbamate (5 g, 28.57 mmol) in dichloromethane (200 mL) was added triphenylphosphine (11.52 g, 42.85 mmol) followed by carbon tetrabromide (14.22 g, 42.85 mmol) at 0° C. The reaction mixture was stirred at rt for 18 h while monitoring by TLC. The solvent was removed under reduced pressure and the residue was purified by column chromatography (60-120 mesh silica gel) using 5-10% ethyl acetate in pet-ether to give tert-butyl 3-bromopropylcarbamate (4.5 g, 66.46%) as a light-brown liquid. 1H NMR (400 MHz, CDCl3) δ ppm 4.63 (1H, s), 3.45-3.42 (2H, t, J=6.4 Hz), 3.29-3.24 (2H, q, J=6.4 Hz), 2.08-2.01 (2H, m), 1.44 (9H, s).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography (60-120 mesh silica gel)

Sources & evidence

ORD record
ord-83a97f5c621f4600ae8a97f04bc86172
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

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