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

HRID 712072Notes

Reaction equation

HRID 712072 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>[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)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl 3-thienylcarbamate (from Ark Pharm, 3.97 g, 19.9 mmol) in methylene chloride (190 mL) was added N-bromosuccinimide (3.54 g, 19.9 mmol) portionwise. The resulting mixture was heated at 40° C. for 20 min. The reaction solution was concentrated and the precipitate was filtered and the filtrate was purified with flash chromatography (eluting with a gradient of 0-10% ethyl acetate in hexanes) to give the desired product as white solid. LCMS calculated for C5H5BrNO2S (M+H−t−Bu)+: m/z=221.9. Found: 221.8.

Workup

  1. concentrationThe reaction solution was concentrated
  2. filtrationthe precipitate was filtered
  3. customthe filtrate was purified with flash chromatography (
  4. washeluting with a gradient of 0-10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e9809d3cd4e34f498ae4d2eaed7a6d08
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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