N-bromobutanimide → HCID 18925573, compound

HRID 1941014Notes

Reaction equation

HRID 1941014 reaction equation
[CH3:1][C:2]12[CH2:17][CH:5]([C:6]3([CH3:16])[C:10]1([CH3:11])[C:9]1[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=1[O:7]3)[CH2:4][CH2:3]2.[Br:18]N1C(=O)CCC1=O>O1CCCC1.CN(C)C=O>[Br:18][C:13]1[CH:14]=[CH:15][C:8]2[O:7][C:6]3([CH3:16])[CH:5]4[CH2:17][C:2]([CH3:1])([C:10]3([CH3:11])[C:9]=2[CH:12]=1)[CH2:3][CH2:4]4

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 187895091,2,3,4,4a,9b-Hexahydro-1,4a,9b-trimethyl-1,4-methanodibenzofuran

Product 1

HCID 18925573HCID 18925573, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

11.42 g (50 mmol) of (-)-1,2,3,4-tetra-hydro-1,4a,9b-trimethyl-1,4-methanodibenzofuran obtained in Example 1 were dissolved in 110 ml of tetrahydrofuran and were treated dropwise with a solution containing 8.9 g of N-bromosuccinimide (NBS) in 50 ml of dimethylformamide (DMF). The reaction mixture was maintained under stirring at room temperature for 2 h, 30 min, and was then poured into ice-cold water and extracted with 500 ml of ethyl ether. After rinsing with water, drying over magnesium sulfate, filtering and evaporating, 13.8 g (90%) of the expected derivative, melting at 119.8° C., were isolated after chromatography on silica in hexane.

Workup

  1. additionwere treated dropwise with a solution
  2. temperatureThe reaction mixture was maintained
  3. additionwas then poured into ice-cold water
  4. extractionextracted with 500 ml of ethyl ether
  5. washAfter rinsing with water
  6. dry with materialdrying over magnesium sulfate
  7. filtrationfiltering
  8. customevaporating
  9. custom13.8 g (90%) of the expected derivative, melting at 119.8° C., were isolated after chromatography on silica in hexane

Sources & evidence

ORD record
ord-daf370f3f10e4100bca7356c904b881d
Source dataset
uspto-grants-1997_12
Patent number
US05702710

Reaction notes

Loading…