Chloroform → HCID 18925573, compound

HRID 1289143Notes

Reaction equation

HRID 1289143 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.C(Cl)(Cl)Cl>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

6

Reactant 3

HCID 6212ChloroformHCID 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-tetrahydro1,4a,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 medium was maintained under stirring at room temperature for 2 h, 30 min, then poured into ice-cold water and extracted with 500 ml of ethyl ether. After rinsing with water, drying over magnesium sulfate, filtration and evaporation, 13.8 g (90w) of the expected compound, melting at 119.8° C., were isolated after chromatography on silica in hexane; αD =+4.60 (c=1, chloroform).

Workup

  1. additionwere treated dropwise with a solution
  2. temperatureThe reaction medium was maintained
  3. additionpoured into ice-cold water
  4. extractionextracted with 500 ml of ethyl ether
  5. washAfter rinsing with water
  6. dry with materialdrying over magnesium sulfate, filtration and evaporation, 13.8 g (90w) of the expected compound, melting at 119.8° C.
  7. customwere isolated after chromatography on silica in hexane

Sources & evidence

ORD record
ord-9694eb76f01946be8e0ff3ffb40fea54
Source dataset
uspto-grants-1998_05
Patent number
US05747530

Reaction notes

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