Toluene → HCID 67354151, compound

HRID 1424781Notes

Reaction equation

HRID 1424781 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[C:17](OS(C(F)(F)F)(=O)=O)=[CH:16][C:11]=3[C:12]=2[C:13]([O-:15])=[O:14])=[CH:4][CH:3]=1.[F-].[K+].[Na+].[Br-].[CH:35]1(B(O)O)[CH2:37][CH2:36]1.[C:41]1(C)C=CC=C[CH:42]=1>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.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[C:17]([CH:35]4[CH2:37][CH2:36]4)=[CH:16][C:11]=3[C:12]=2[C:13]([O:15][CH2:41][CH3:42])=[O:14])=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 253881Sodium BromideHCID 522689Potassium FluorideHCID 2760897Cyclopropylboronic acidHCID 86696005HCID 86696005, compound

Product 1

HCID 67354151HCID 67354151, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-(4-chlorophenyl)-6-nitro-5-(trifluoromethylsulfonyloxy)benzofuran-3-carboxylate (10 g, 18 mmol), KF (4.64 g, 79.9 mmol), NaBr (2.48 g, 24 mmol), cyclopropylboronic acid (3.2 g, 37 mmol), and Pd(Ph3P)4 (1.33 g, 1.15 mmol) were added toluene (130 mL) and water (2.8 mL). The reaction flask was evacuated for ˜3 minutes then filled with nitrogen. The reaction mixture was refluxed under nitrogen for 20 hrs then cooled to ambient temperature. The reaction mixture was diluted with EtOAc (150 mL), washed with water (3×200 mL), brine (200 mL), dried with anhydrous sodium sulfate, decanted, and concentrated under reduced pressure. The residue was purified by column chromatography (petroleum ether/ethyl acetate=30/1-10/1) to afford ethyl 2-(4-chlorophenyl)-5-cyclopropyl-6-nitrobenzofuran-3-carboxylate as a yellow solid (7.9 g, 99%).

Workup

  1. customThe reaction flask was evacuated for ˜3 minutes
  2. additionthen filled with nitrogen
  3. temperatureThe reaction mixture was refluxed under nitrogen for 20 hrs
  4. additionThe reaction mixture was diluted with EtOAc (150 mL)
  5. washwashed with water (3×200 mL), brine (200 mL)
  6. dry with materialdried with anhydrous sodium sulfate
  7. customdecanted
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography (petroleum ether/ethyl acetate=30/1-10/1)

Sources & evidence

ORD record
ord-73c029e2d2a248cc8b85fdb90305d83d
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

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