Benzyl chloroformate → Benzyl (3-bromophenyl)carbamate

HRID 1713263Notes

Reaction equation

HRID 1713263 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[OH-].[Na+].Cl[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:12](=[O:13])[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 115623-BromoanilineHCID 14798Sodium Hydroxide

Product 1

HCID 60102049Benzyl (3-bromophenyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-bromoaniline (0.500 g), 2 mol/L aqueous sodium hydroxide (2.18 mL) and tetrahydrofuran (3.63 mL) was added dropwise benzyl chloroformate (0.498 mL), and the resulting mixture was stirred at room temperature for 3.5 hours. The reaction mixture was partitioned between ethyl acetate (35 mL) and water (10 mL). The organic layer was washed with brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=8/1) to give the title compound (0.897 g).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (35 mL) and water (10 mL)
  2. washThe organic layer was washed with brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-e46ca1ed48af4141a168089f8ec32ea8
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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