Pentane → 2-Bromo-5-[(4-fluorophenyl)methyl]furan

HRID 52165Notes

Reaction equation

HRID 52165 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[Br:14]Br.CCCCC>CN(C=O)C.C(Cl)Cl>[Br:14][C:11]1[O:10][C:9]([CH2:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 8003PentaneHCID 24408BromineHCID 199632912-(4-Fluorophenylmethyl)furan

Product 1

HCID 199632922-Bromo-5-[(4-fluorophenyl)methyl]furan

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a -30° C. solution of 2-(4-fluorophenylmethyl)furan, prepared as in step 1 (32.0 g, 0.18 mol) in anhydrous DMF (60 mL) was added a solution of bromine (28.9 g, 0.18 mol) in CH2Cl2 (250 mL). The mixture was stirred for 0.5 hours at -10° C. and poured into pentane (1600 mL). The penlane was then decanted from the dark colored insoluble layer. Evaporation of the pentane gave the crude product which was purified by flash-chromatography on silica gel eluting with penlane to provide 2-Bromo-5-(4-fluorophenylmethyl)furan as a cream colored solid in a yield of 8.87 g (19.2%).

Workup

  1. customThe penlane was then decanted from the dark colored insoluble layer
  2. customEvaporation of the pentane
  3. customgave the crude product which
  4. customwas purified by flash-chromatography on silica gel eluting with penlane

Sources & evidence

ORD record
ord-40d8dc6fd6484217a80fc457c3d86bd5
Source dataset
uspto-grants-1997_04
Patent number
US05616596

Reaction notes

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