2,5-Dimethoxytetrahydrofuran → HCID 22473584, compound

HRID 2184040Notes

Reaction equation

HRID 2184040 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([CH:8]=1)[NH2:7].CO[CH:12]1[CH2:16][CH2:15][CH:14](OC)O1>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([N:7]2[CH:12]=[CH:16][CH:15]=[CH:14]2)[CH:8]=1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 27694075-Bromo-2-fluoroaniline

Product 1

HCID 22473584HCID 22473584, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5-bromo-2-fluoroaniline (prepared according to the procedure of Roe et al. in J. Org. Chem., 1956, 21, 28-29) (200 mg, 1.05 mmol) and 2,5-dimethoxytetrahydrofuran (171 μl, 1.32 mmol) in glacial acetic acid (1.5 ml) was heated at 130° C. for 20 min and then concentrated under reduced pressure. The residue was dissolved in dichloromethane and pre-adsorbed onto silica. Purification by chromatography on silica gel eluting with 10% diethyl ether in isohexane yielded 1-(5-bromo-2-fluorophenyl)-1H-pyrrole (335 mg, 99%): δH (360 MHz, CDCl3) 7.53 (1H, dd, J 7 and 3), 7.33 (1H, ddd, J 9, 4 and 3), 7.10 (1H, dd, J 11 and 9), 7.04-6.95 (2H, m), 6.36 (2H, t, J 2).

Workup

  1. customprepared
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane and pre-adsorbed onto silica
  4. customPurification by chromatography on silica gel eluting with 10% diethyl ether in isohexane

Sources & evidence

ORD record
ord-0e5d5982185942feb9fdc7e0fb660370
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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