N-bromobutanimide → tert-Butyl (2-bromothiophen-3-yl)carbamate

HRID 1773313Notes

Reaction equation

HRID 1773313 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][C:8]1[CH:12]=[CH:11][S:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Br:14]N1C(=O)CCC1=O>ClCCl>[C:1]([O:5][C:6](=[O:13])[NH:7][C:8]1[CH:12]=[CH:11][S:10][C:9]=1[Br:14])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 736476tert-Butyl thiophen-3-ylcarbamate

Product 1

HCID 13164363tert-Butyl (2-bromothiophen-3-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

According to the method described in WO2005070916, A boiling solution of tert-Butyl-N-(thiophen-3-yl)carbamate (5.32 g, 26.70 mmol) in dichloromethane (260 ml) was treated portionwise with N-bromo-succinimide (4.73 g, 26.70 mmol) under vigorous stirring. After addition was complete, the heating bath temperature was raised to 65° C. and maintained for 20 minutes before allowing the reaction to cool to room temperature. The reaction mixture was washed with water, dried (MgSO4), filtered, and concentrated. Elution through a flash column (silica gel 60, 230-400 mesh, 4:1 hexanes:EtOAc) gave a clear oil which crystallized on standing (7.24 g, 97%).

Workup

  1. additionAfter addition
  2. temperaturemaintained for 20 minutes
  3. customthe reaction
  4. temperatureto cool to room temperature
  5. washThe reaction mixture was washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washElution through a flash column (silica gel 60, 230-400 mesh, 4:1 hexanes:EtOAc)
  10. customgave a clear oil which
  11. customcrystallized

Sources & evidence

ORD record
ord-c30d6d213ad74db3a75f214aab0d01fa
Source dataset
uspto-grants-2016_02
Patent number
US09255096B1

Reaction notes

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