Potassium Phosphate, Tribasic → HCID 90418489, compound

HRID 2177365Notes

Reaction equation

HRID 2177365 reaction equation
Br[C:2]1[S:3][C:4]([CH3:16])=[C:5]([C:12]([F:15])([F:14])[F:13])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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.O1CCOCC1>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[S:3][C:4]([CH3:16])=[C:5]([C:12]([F:15])([F:14])[F:13])[C:6]=2[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 742994-Chlorophenylboronic acidHCID 90418452HCID 90418452, compound

Product 1

HCID 90418489HCID 90418489, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed ethyl 2-bromo-5-methyl-4-(trifluoromethyl)thiophene-3-carboxylate (250 mg, 0.79 mmol, 1.00 equiv), (4-chlorophenyl)boronic acid (185 mg, 1.18 mmol, 1.50 equiv), K3PO4 (620 mg, 2.92 mmol, 3.71 equiv), Pd(PPh3)4 (73 mg, 0.06 mmol, 0.08 equiv), dioxane (20 mL). The resulting solution was stirred overnight at 90° C. The solids were filtered out. The filtrate was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/5). The collected fractions were combined and concentrated under vacuum. This resulted in 200 mg (69%) of ethyl 2-(4-chlorophenyl)-5-methyl-4-(trifluoromethyl)thiophene-3-carboxylate as colorless oil.

Workup

  1. customInto a 100-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. filtrationThe solids were filtered out
  4. concentrationThe filtrate was concentrated under vacuum
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 200 mg (69%) of ethyl 2-(4-chlorophenyl)-5-methyl-4-(trifluoromethyl)thiophene-3-carboxylate as colorless oil

Sources & evidence

ORD record
ord-7d4324f000d84bceba1e1c1dc38c25f0
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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