Sodium Carbonate → 2-(4-Fluorophenyl)thiophene

HRID 2172699Notes

Reaction equation

HRID 2172699 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[F:7][C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:2]2[S:3][CH:4]=[CH:5][CH:6]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 138512-BromothiopheneHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 218947832-(4-Fluorophenyl)thiophene

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2-bromothiophene (233.0 g, 1.43 mol), 4-fluorophenyl boronic acid (200.0 g, 1.43 mol), bis(triphenylphosphine)palladium(II) dichloride (10.0 g, 14.2 mmol) and aqueous Na2CO3 (454.5 g, 4.3 mol in 1.5 L of H2O) in 1,2-dimethoxyethane (2 L) was stirred at 75-80° C. (internal temperature) for 2 hours. The resulting mixture was cooled to room temperature and then stirred overnight. The solid was separated and discarded. The liquid was washed with water (2×500 mL). The combined aqueous layer was extracted with diethylether (2×500 mL). The combined organic layers were then dried over NaCl, concentrated and purified by flask distillation to yield the title compound as a white solid.

Workup

  1. customThe solid was separated
  2. washThe liquid was washed with water (2×500 mL)
  3. extractionThe combined aqueous layer was extracted with diethylether (2×500 mL)
  4. dry with materialThe combined organic layers were then dried over NaCl
  5. concentrationconcentrated
  6. custompurified by flask
  7. distillationdistillation

Sources & evidence

ORD record
ord-a753713bec1e40d8882841c497ac1684
Source dataset
uspto-grants-2015_06
Patent number
US09056850B2

Reaction notes

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