Sodium Carbonate → HCID 21838297, compound

HRID 1740311Notes

Reaction equation

HRID 1740311 reaction equation
Br[C:2]1[CH:6]=[C:5]([Cl:7])[S:4][C:3]=1[Cl:8].[CH3:9][O:10][C:11]([C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:18]=1)=[O:12].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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.C(OCC)(=O)C>[Cl:8][C:3]1[S:4][C:5]([Cl:7])=[CH:6][C:2]=1[C:15]1[CH:14]=[C:13]([C:11]([O:10][CH3:9])=[O:12])[CH:18]=[C:17]([CH:16]=1)[C:19]([O:21][CH3:22])=[O:20]

Participants

8

Reactant 4

HCID 10340Sodium Carbonate2×HCID 433294Lithium ChlorideHCID 5219253-Bromo-2,5-dichlorothiopheneHCID 19363104[3,5-Bis(methoxycarbonyl)phenyl]boronic acid

Product 1

HCID 21838297HCID 21838297, compoundYield 58.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3-bromo-2,5-dichlorothiophene (0.30 g), [3,5-bis(methoxycarbonyl)phenyl]-dihydroxyborane (0.37 g), lithium chloride (0.164 g), tetrakis(triphenylphosphine)palladium(0) (0.0747 g) and 2M aqueous sodium carbonate solution (1.55 ml) in 1,2-dimethoxyethane (3.6 ml) was heated at 85° C. and stirred vigorously for 4 hours under nitrogen. The reaction mixture was cooled to room temperature and to the mixture was added ethyl acetate (20 ml) and 2M sodium carbonate solution (20 ml). The layers were separated, and the organic layer was washed successively with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (20:1). The fractions containing the desired product were collected and evaporated in vacuo to give dimethyl 5-(2,5-dichlorothiophen-3-yl)isophthalate (0.26 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature and to the mixture
  2. customThe layers were separated
  3. washthe organic layer was washed successively with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (20:1)
  7. additionThe fractions containing the desired product
  8. customwere collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-f1f2b81f1a144d5b929c69cf4ab2d083
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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