N-bromobutanimide → HCID 67775687, compound

HRID 2285327Notes

Reaction equation

HRID 2285327 reaction equation
[CH:1]1[C:13]2[C:12]3[O:11][C:10]4[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=4[C:8]=3[CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:18]N1C(=O)CCC1=O>CN(C)C=O.O>[Br:18][C:6]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:13]=2[C:12]2[O:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[C:8]=2[CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67460Benzo[b]naphtho[2,1-d]furan

Product 1

HCID 67775687HCID 67775687, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

32.7 g of benzo[b]naphtho[2,1-d]furan was dissolved in 300 mL of N,N-dimethylformamide. Then, 50 mL of a N,N-dimethylformamide solution of 28.0 g of N-bromosuccinimide was added, and the resulting reaction solution was stirred with heating at 60° C. for 5 hours. After cooling to room temperature, the reaction solution was poured in 2 L of water. Solids thus obtained were sequentially washed with methanol, water and methanol. The resulting crude product was purified by means of silica gel column chromatography, whereby 36.5 g (yield: 82%) of 5-bromobenzo[b]naphtho[2,1-d]furan was obtained.

Workup

  1. customthe resulting reaction solution
  2. temperatureAfter cooling to room temperature
  3. customSolids thus obtained
  4. washwere sequentially washed with methanol, water and methanol
  5. customThe resulting crude product was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-c58207d89b424e92a6ce430f99c0c6d9
Source dataset
uspto-grants-2015_09
Patent number
US09147847B2

Reaction notes

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