Triethylamine → tert-Butyl 3-bromobenzylcarbamate

HRID 390622Notes

Reaction equation

HRID 390622 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7].[C:11](OC([O-])=O)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(N(CC)CC)C>ClCCl>[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH:7][C:11](=[O:12])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27249803-Bromobenzylamine hydrochlorideHCID 22064466Tert-butyldicarbonate

Product 1

HCID 11033439tert-Butyl 3-bromobenzylcarbamateYield 102.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 25 g (110 mmol) of 3-bromobenzylamine hydrochloride and 24.5 g (110 mmol) of tert-butyl dicarbonate in 250 mL of dichloromethane in the presence of 15.6 mL (110 mmol) of triethylamine is stirred at room temperature for 16 hours. The reaction medium is washed with water, the phases are separated by settling and the organic phase is dried over sodium sulfate. The solvent is evaporated off and 32.4 g (100%) of tert-butyl (3-bromobenzyl)carbamate are obtained in the form of crystals.

Workup

  1. washThe reaction medium is washed with water
  2. customthe phases are separated
  3. dry with materialthe organic phase is dried over sodium sulfate
  4. customThe solvent is evaporated off

Sources & evidence

ORD record
ord-e4f9b643759e42af80358c77fd71f19e
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

Loading…