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Potassium Carbonate → Methyl 7-(4-chlorophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate

HRID 1978572
Notes
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Reaction equation

HRID 1978572 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:11](=[O:13])(=[O:12])[CH2:10][CH2:9][C:8]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][C:6]=2[CH:18]=1.B([O-])([O-])O[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:2]2[CH:3]=[CH:4][C:5]3[S:11](=[O:13])(=[O:12])[CH2:10][CH2:9][C:8]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][C:6]=3[CH:18]=2)=[CH:22][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21995732Methyl 7-bromo-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylateHCID 867561664-Chlorophenyl borate

Product 1

HCID 21995682Methyl 7-(4-chlorophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylateYield 60.8%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 86587398Ethanol toluene waterSolvent

Procedure

Under argon atmosphere, methyl 7-bromo-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.70 g), a mixture of 4-chlorophenyl borate (0.38 g) and potassium carbonate (0.59 g) in toluene/ethanol/water (20/2/2 ml) was stirred at room temperature for 1 hour. To the mixture was added tetrakistriphenylphosphinepalladium (0.12 g), and the mixture was refluxed for 20 hours, cooled, extracted with ethyl acetate, washed with saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified with column chromatography (ethyl acetate/hexane=1:1) and recrystallized from ethyl acetate/hexane to give to give pale yellow crystals of methyl 7-(4-chlorophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (466 mg).

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with column chromatography (ethyl acetate/hexane=1:1)
  8. customrecrystallized from ethyl acetate/hexane
  9. customto give

Sources & evidence

ORD record
ord-0fe75ca1246f494ead7e2afd10aabb63
Source dataset
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06235771B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes