Bromine → HCID 68564868, compound

HRID 41682Notes

Reaction equation

HRID 41682 reaction equation
[CH2:1]([C:3]1[C:4]([CH:9]2[C:17](=[O:18])[CH:16]3[CH:11]([CH:12]4[O:19][CH:15]3[CH2:14][CH2:13]4)[C:10]2=[O:20])=[C:5]([CH3:8])[S:6][CH:7]=1)[CH3:2].[Br:21]Br>C(Cl)Cl>[Br:21][C:7]1[S:6][C:5]([CH3:8])=[C:4]([CH:9]2[C:17](=[O:18])[CH:16]3[CH:11]([CH:12]4[O:19][CH:15]3[CH2:14][CH2:13]4)[C:10]2=[O:20])[C:3]=1[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 687734264-(4-Ethyl-2-methyl-thiophen-3-yl)-10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione

Product 1

HCID 68564868HCID 68564868, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-(4-ethyl-2-methyl-thiophen-3-yl)-10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione (73 mg, 0.25 mmol) in DCM (2 ml), at 0° C., is added bromine (26 μl, 0.5 mmol) in one portion, and the reaction allowed to warm to ambient and stirred at room temperature for 3 hours. The reaction is concentrated in vacuo, re-dissolved in methanol (10 ml), potassium carbonate (250 mg) added and the resulting suspension stirred at room temperature for a further 17 hours. The reaction is quenched by the addition if 2N aqueous HCl (10 ml) and extracted with DCM (2×10 ml). The combined organics extracts are dried, filtered, concentrated in vacuo, and purified by flash chromatography on silica gel to give 4-(5-bromo-4-ethyl-2-methyl-thiophen-3-yl)-10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione as a brown solid (43 mg).

Workup

  1. temperatureto warm to ambient and
  2. concentrationThe reaction is concentrated in vacuo
  3. dissolutionre-dissolved in methanol (10 ml)
  4. additionpotassium carbonate (250 mg) added
  5. stirringthe resulting suspension stirred at room temperature for a further 17 hours
  6. customThe reaction is quenched by the addition if 2N aqueous HCl (10 ml)
  7. extractionextracted with DCM (2×10 ml)
  8. customThe combined organics extracts are dried
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e943f19e4ed746d0b710538920cedff3
Source dataset
uspto-grants-2013_09
Patent number
US08530667B2

Reaction notes

Loading…