Carbon tetrabromide → methyl 7-(benzenesulfonylmethyl)-4H-furo[2,3-c]chromene-6-carboxylate

HRID 1778339Notes

Reaction equation

HRID 1778339 reaction equation
C(Br)(Br)(Br)Br.[C:6]1([S:12]([CH2:15][C:16]2[C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20](O)[C:19]([C:27]3[CH:31]=[CH:30][O:29][C:28]=3[CH2:32][OH:33])=[CH:18][CH:17]=2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:6]1([S:12]([CH2:15][C:16]2[C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20]3[C:19]([C:27]4[CH:31]=[CH:30][O:29][C:28]=4[CH2:32][O:33]3)=[CH:18][CH:17]=2)(=[O:14])=[O:13])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66685310Methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-(2-hydroxymethylfuran-3-yl)-benzoate2×

Product 1

HCID 66685555methyl 7-(benzenesulfonylmethyl)-4H-furo[2,3-c]chromene-6-carboxylateYield 19.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbon tetrabromide (0.116 g) was added to a solution of methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-(2-hydroxymethylfuran-3-yl)-benzoate (Intermediate 19, 0.1 g) and triphenyl phosphine (0.09 g) in DCM (3 mL) and the resultant solution was stirred at room temperature for 2 hours. The mixture was evaporated to dryness and the residue was dissolved in DMF (2 mL) and cesium carbonate (0.163 g) was added. The mixture was stirred for 1 hour at room temperature, then at 50° C. for 15 minutes. After cooling, the mixture was partitioned between ethyl acetate and water, the organic layer was separated, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane (25%) to give methyl 7-(benzenesulfonylmethyl)-4H-furo[2,3-c]chromene-6-carboxylate (0.019 g).

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in DMF (2 mL)
  3. additioncesium carbonate (0.163 g) was added
  4. waitat 50° C. for 15 minutes
  5. temperatureAfter cooling
  6. customthe mixture was partitioned between ethyl acetate and water
  7. customthe organic layer was separated
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customThe filtrate was evaporated to dryness
  11. customthe residue was purified by chromatography on silica
  12. washeluting with a mixture of ethyl acetate and cyclohexane (25%)

Sources & evidence

ORD record
ord-7786cfb17f7742e68922bfac2c98c2f3
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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