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

HRID 2211663Notes

Reaction equation

HRID 2211663 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][NH2:6].[O:11](C(OC(C)(C)C)=O)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=O>C(Cl)Cl.[OH-].[Na+]>[C:15]([O:14][C:12]([NH:6][CH2:5][C:4]1[CH:7]=[CH:8][C:9]([F:10])=[C:2]([Br:1])[CH:3]=1)=[O:11])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 2724902(3-Bromo-4-fluorophenyl)methanamine

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 (10 g, 41 mmol) and TEA (14 mL, 104 mmol) in CH2Cl2 was added BOC2O (9.1 g, 41 mmol). The resulting solution was stirred for 16 h at RT, then diluted with aq. 1 N NaOH and CH2Cl2. The organic layer was separated, washed with brine, dried over Na2SO4, and concentrated to give (tert-butoxy)-N-[(3-bromo-4-fluorophenyl)methyl]carboxamide.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a7caacd66dac47bbb96e30a05676db55
Source dataset
uspto-grants-2006_09
Patent number
US07101868B2

Reaction notes

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