Furan → 2-(4-Fluorophenylmethyl)furan

HRID 1975747Notes

Reaction equation

HRID 1975747 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])CCC.CCCCCC.[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1.[Cl-].[NH4+]>C1COCC1.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.CCOCC>[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:20][CH:19]=1

Participants

9

Reactant 5

HCID 8029FuranHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 680214-Fluorobenzyl bromideHCID 178418339Butyllithium

Product 1

HCID 199632912-(4-Fluorophenylmethyl)furanYield 81.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of furan (13.6 g, 0.20 mol) in a mixture of anhydrous ether (230 mL) and anhydrous THF (70 mL) under nitrogen was added a 2.5M solution of n-butyllithium in hexane (54.0 mL, 0.134 mol). The mixture was stirred at 0° C. for 1.5 hours and then transferred by cannula to a stirred -78° C. solution of 4-fluorobenzyl bromide (23.6 g, 0.125 mol) and tetrakis(triphenylphosphine)palladium (0) (1.25 g, 0.001 mol) in anhydrous THF (200 mL). The transfer was made under nitrogen over a period of 30-40 minutes. The reaction mixture was stirred at ambient temperature overnight, saturated aqueous solution of ammonium chloride was added and the mixture extracted with ether. The ether layer was dried (MgSO4), concentrated in vacuo and the residue distilled at reduced pressure to give the title compound as a colorless oil (17.89 g, 81%). b.p. 57°-62° C. at 0.5-0.7 mm-Hg.

Workup

  1. customtransferred by cannula to a stirred -78° C.
  2. waitThe transfer was made under nitrogen over a period of 30-40 minutes
  3. stirringThe reaction mixture was stirred at ambient temperature overnight
  4. extractionthe mixture extracted with ether
  5. dry with materialThe ether layer was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. distillationthe residue distilled at reduced pressure

Sources & evidence

ORD record
ord-8c2ad678073547b5970d83ec19c1d054
Source dataset
uspto-grants-1994_02
Patent number
US05288751

Reaction notes

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