Di-tert-butyl dicarbonate → Tert-butyl (2-bromo-5-methoxybenzyl)carbamate

HRID 1712953Notes

Reaction equation

HRID 1712953 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][NH2:11].[O:12](C(OC(C)(C)C)=O)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][NH:11][C:13](=[O:12])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 24691009(2-Bromo-5-methoxyphenyl)methanamine

Product 1

HCID 22930485Tert-butyl (2-bromo-5-methoxybenzyl)carbamateYield 96.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-bromo-5-methoxyphenyl)methanamine (3.2 mmol) in DCM (15 mL) was added BOC2O (3.2 mmol). The reaction mixture was allowed to stir at rt overnight and then concentrated. The residue was purified by column chromatography to give tert-butyl (2-bromo-5-methoxybenzyl)carbamate (3.1 mmol, 95%).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-70f8d574887042aabeef4e1eeace8023
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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