Diethyl Ether → HCID 58466211, compound

HRID 335798Notes

Reaction equation

HRID 335798 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([I:16])=[CH:9][CH:10]=3)[C:5](=O)[C:4]=2[CH:3]=1.[CH3:18][Mg]Br.CCOCC.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C(Cl)Cl.C1COCC1>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([I:16])=[CH:9][CH:10]=3)[C:5](=[CH2:18])[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57475644HCID 57475644, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58466211HCID 58466211, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 500 ml RB flask was charged with 2-bromo-7-iodo-9H-xanthen-9-one (16.030 g, 40.0 mmol) and THF (150 mL). The mixture was stirred for 10 min at RT and the resulting suspension was placed in water-ice bath for another 10 min. Methylmagnesium bromide, 3.0 M in Et2O (20.0 ml, 60.0 mmol) was added dropwise. After 1 hr, the mixture was carefully quenched with sat NH4Cl (150 mL) at 0° C. and diluted with EtOAc. The organic layer was washed with brine, dried with sodium sulfate, and concentrated in vacuo. The material was dissolved in 100 mL of methylene chloride, treated with PPTS (0.201 g, 0.800 mmol), and heated to reflux for 2 hr. The mixture was cooled to RT, diluted with methylene chloride, and washed with saturated sodium bicarbonate and brine. The organic fraction was dried over sodium sulfate and concentrated in vacuo to afford crude 2-bromo-7-iodo-9-methylene-9H-xanthene as a light orange solid that was advanced without further purification. MS: MH+=399.0/401.0.

Workup

  1. customfor another 10 min
  2. waitAfter 1 hr
  3. customthe mixture was carefully quenched with sat NH4Cl (150 mL) at 0° C.
  4. additiondiluted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated in vacuo
  8. dissolutionThe material was dissolved in 100 mL of methylene chloride
  9. temperatureheated
  10. temperatureto reflux for 2 hr
  11. temperatureThe mixture was cooled to RT
  12. washwashed with saturated sodium bicarbonate and brine
  13. dry with materialThe organic fraction was dried over sodium sulfate
  14. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb79024cb9824e7780df71e5000bd4a6
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

Loading…