2-[[(4-Bromophenyl)imino]methyl]phenol → HCID 14492606, compound

HRID 897614Notes

Reaction equation

HRID 897614 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]=[CH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[OH:24])=[CH:12][CH:11]=1>CS(C)=O>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][CH:17]2[CH2:4][O:24][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]2=3)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 134482-[[(4-Bromophenyl)imino]methyl]phenolHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)

Product 1

HCID 14492606HCID 14492606, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A 60% dispersion of sodium hydride in mineral oil (0.145 g, 0.00362 mol) was added to a solution of trimethylsulfoxonium iodide (0.8 g, 0.00362 mol) in anhydrous dimethylsulfoxide (10 mL) and the resulting mixture was stirred under an atmosphere of nitrogen for 10 min. A solution of 2-{[(4-bromophenyl)imino]methyl}phenol (0.4 g, 0.00145 mol) in anhydrous dimethylsulfoxide (5 mL) was added dropwise and the resulting mixture was stirred at ambient temperature for 2.5 hours. It was poured into ice-cold water (100 mL) and extracted with diethyl ether (2×50 mL). The combined organic extracts were dried with magnesium sulfate and concentrated under reduced pressure to yield N-(4-bromophenyl)-N-(2,3-dihydrobenzo[b]furan-3-yl)amine (0.321 g, 0.0011 mol) as an off-white solid.

Workup

  1. stirringthe resulting mixture was stirred at ambient temperature for 2.5 hours
  2. extractionextracted with diethyl ether (2×50 mL)
  3. dry with materialThe combined organic extracts were dried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6a89b58f9c0a45e2b5a994eff89c5687
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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