Di-tert-butyl dicarbonate → [(3-Bromo-4-fluorophenyl)methyl]-carbamic acid tert-butyl ester

HRID 2211659Notes

Reaction equation

HRID 2211659 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[F:11])[CH2:6][NH2:7].[O:12](C(OC(C)(C)C)=O)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=O>C(Cl)Cl.[OH-].[Na+]>[C:13]([NH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:10]([F:11])=[C:3]([Br:2])[CH:4]=1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:12]

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 27249011-(3-Bromo-4-fluorophenyl)methanamine hydrochloride

Product 1

HCID 21961437[(3-Bromo-4-fluorophenyl)methyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3-bromo-4-fluorobenzylamine hydrochloride (10 g, 42 mmol) and TEA (10.5 g, 103 mmol) in 200 mL of CH2Cl2 was added BOC2O (9.1 g, 42 mmol) at RT. The resulting solution was stirred for 16 h. The solution was diluted with aq. 1 N NaOH and CH2Cl2. The organic layer was washed with brine, dried over Na2SO4, and concentrated to give N-Boc-(3-bromo-4-fluoro-benzyl)amine. MS (ES+): 305 (M+H)+; (ES−): 303 (M−H). Calc'd C12H15BrFNO2-304.16.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1135b9cebe0c405697cd5feb0d493643
Source dataset
uspto-grants-2006_09
Patent number
US07101868B2

Reaction notes

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