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

HRID 641619Notes

Reaction equation

HRID 641619 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:2]1.[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:14][C:2]1[S:1][CH:5]=[CH:4][C:3]=1[NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11]

Participants

4

Reactant 2

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

Product 1

HCID 13164363tert-Butyl (2-bromothiophen-3-yl)carbamateYield 96%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
23 °C

Procedure

Tert-butyl thien-3-ylcarbamate (37 g, 0.19 mol) and N-bromosuccinimide (33 g, 0.19 mol) were combined in carbon tetrachloride (900 mL) and heated at reflux for 3 h. At this time, the mixture was cooled to 23° C. and filtered. The filtrate was washed with water (5×900 mL) to remove succinimide, dried (Na2SO4), and concentrated in vacuo to give the title compound (50 g, 96%, m.p. 68-70° C.) as a tan solid which was pure enough for further use.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. filtrationfiltered
  4. washThe filtrate was washed with water (5×900 mL)
  5. customto remove succinimide
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6aac4db309d848f9a9610ab66521aac6
Source dataset
uspto-grants-2010_04
Patent number
US07696221B2

Reaction notes

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