N-bromobutanimide → HCID 71133722, compound

HRID 1625170Notes

Reaction equation

HRID 1625170 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:18][CH:9]3[O:10][C:11]4[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=4[CH:8]3[C:6]=2[CH:7]=1.C1C(=O)N([Br:26])C(=O)C1.[Al]>CN(C=O)C>[Br:26][C:4]1[C:5]2[O:18][CH:9]3[CH:8]([C:6]=2[CH:7]=[C:2]([CH3:1])[CH:3]=1)[C:12]1[CH:13]=[CH:14][C:15]([CH3:17])=[CH:16][C:11]=1[O:10]3

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 5359268AluminumHCID 71133682HCID 71133682, compound

Product 1

HCID 71133722HCID 71133722, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The backbone 2,8-dimethyl-5a,10b-dihydrobenzofuro-[2,3-b]benzofuran (1.5 g, 6.3 mmol) and NBS (2.016 g, 11.3 mmol) are dissolved in DMF (100 mL) and stirred at RT for 1 day (flask is covered with aluminium foil). The conversion is monitored by GC/MS. After three days, a mixture of the monobrominated product, the dibrominated product, and the unmodified backbone (monobromo/dibromo/backbone) is formed, in a 75/23/2 ratio, based on weight percents. The solvent is evaporated to dryness and the solid is washed with water and extracted with dichloromethane. The dichloromethane solution is then dried over MgSO4 and evaporated to dryness. The solid obtained is washed with ethanol to give a white solid (1.5 g, containing a mixture of monobromo/dibromo, 75/25). This product (“bromobackbone”) is used in step (b) without further purification.

Workup

  1. additiona mixture of the monobrominated product
  2. customthe dibrominated product, and the unmodified backbone (monobromo/dibromo/backbone) is formed, in a 75/23/2 ratio
  3. customThe solvent is evaporated to dryness
  4. washthe solid is washed with water
  5. extractionextracted with dichloromethane
  6. dry with materialThe dichloromethane solution is then dried over MgSO4
  7. customevaporated to dryness
  8. customThe solid obtained
  9. washis washed with ethanol
  10. customto give a white solid (1.5 g
  11. additioncontaining
  12. additiona mixture of monobromo/dibromo, 75/25)
  13. customThis product (“bromobackbone”) is used in step (b) without further purification

Sources & evidence

ORD record
ord-81def8ca337a447fa1c5f13289886dfa
Source dataset
uspto-grants-2014_07
Patent number
US08779164B2

Reaction notes

Loading…