Acetone → 9-Bromo-4-oxo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester

HRID 575050Notes

Reaction equation

HRID 575050 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]2[C:8](Br)(Br)[CH2:9][O:10][C:11]3[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:12]=3[C:13]=2[N:14]=1)=[O:4].CC(C)=[O:24]>O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]2[C:8](=[O:24])[CH2:9][O:10][C:11]3[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:12]=3[C:13]=2[N:14]=1)=[O:4]

Participants

4

Reactant 2

HCID 180AcetoneHCID 866930864,4,9-Tribromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester

Product 1

HCID 866930859-Bromo-4-oxo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 4,4,9-Tribromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester (9.0 g, 18.07 mmol) in acetone (250 mL) and water (250 mL) was stirred at room temperature for 4 h. Then the mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc (2×200 mL). The combined organic layers were washed with brine, dried over Na2SO4, concentrated to afford the crude product which was triturated with EtOAc and hexane (EtOAc/hexane=1/5). After filtration, the solid was dried in vacuo to afford compound 9-Bromo-4-oxo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester (5.5 g, 86%) as a light yellow solid.

Workup

  1. customThen the mixture was partitioned between EtOAc and H2O
  2. extractionThe aqueous layer was extracted with EtOAc (2×200 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto afford the crude product which
  7. customwas triturated with EtOAc and hexane (EtOAc/hexane=1/5)
  8. filtrationAfter filtration
  9. customthe solid was dried in vacuo

Sources & evidence

ORD record
ord-1fde194404a645fa8a9a098b5bdb15d2
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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