Carbon tetrabromide → tert-butyl N-(4-bromobutyl)carbamate

HRID 474241

Reaction equation

HRID 474241 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:34]>ClCCl>[Br:34][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 545141tert-Butyl N-(4-hydroxybutyl)carbamate

Product 1

HCID 10868765tert-butyl N-(4-bromobutyl)carbamateYield 63.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of tert-butyl 4-hydroxybutylcarbamate (5 g, 26.41 mmol) in dichloromethane (200 mL) was added triphenylphosphine (10.38 g, 39.61 mmol) followed by carbon tetrabromide (13.15 g, 39.61 mmol) at 0° C. The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was purified by column chromatography (60-120 mesh silica gel) using 10% ethyl acetate in pet-ether to give tert-butyl 4-bromobutylcarbamate (4.2 g, 63.3%) as a light green liquid. 1H NMR (400 MHz, CDCl3) δ ppm 4.53 (1H, s), 3.45-3.41 (2H, m), 3.18-3.13 (2H, m), 1.93-1.83 (2H, m), 1.68-1.61 (2H, m), 1.47 (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-fdfc9428d41b4e47a843a033fe2ee327
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Linked notes

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