Benzene, (3-bromopropoxy)- → HCID 18476852, compound

HRID 2188424Notes

Reaction equation

HRID 2188424 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[O:13]([CH2:20][CH2:21][CH2:22]Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[O:13]([CH2:20][CH2:21][CH2:22][C:10]1[CH:9]=[CH:8][CH:7]=[C:3]2[C:4]([NH:5][C:1](=[O:11])[C:2]=12)=[O:6])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 68522Benzene, (3-bromopropoxy)-HCID 24194345Phthalimide potassium salt

Product 1

HCID 18476852HCID 18476852, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
165 °C

Procedure

A mixture of 7.41 g (40.0 mmol) of potassium phthalimide and 6.30 mL (40.0 mmol) of 3-phenoxypropylbromide in 100 mL DMF was stirred at reflux (165° C.) under N2(g) for 90 min. Mixture was cooled and filtered, filtrate was condensed in vacuo. Residue was recrystallized from 95% ethanol to give 44 (6.68 g, 58%) as a white solid. UV λmax 222 (41700, 95% ETHANOL). 1H NMR (400 MHz, CDCl3) δ 7.85 (m, 2H), 7.72 (m, 2H), 7.24 (t, J=10 Hz, 2H), 6.92 (t, J=7 Hz, 4H), 6.82 (d, J=4 Hz, 2H), 4.03 (t, J=6 Hz, 2H), 3.92 (t, J=4 Hz, 2H), 2.20 (t, J=3 Hz, 2H); 13C NMR (CDCl3) δ 168.7, 134.7, 134.3, 132.6, 129.7, 124.0, 123.6, 121.1, 114.9, 65.9, 35.9, 28.7; IR (drift) 2474 (w), 2431 (w), 2417 (w), 2339 (w), 2305 (w), 1770, 1705 (s), 1600, 1397, 1388, 1249 (s), 1233, 756, 721 (s), 712, cm−1. HRMS (FAB) calcd for C17H15NO3+H1 282.1130, found 282.1129.

Workup

  1. temperatureMixture was cooled
  2. filtrationfiltered
  3. customcondensed in vacuo
  4. customResidue was recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-54f4a9cd5dcb44678f91366a6935a566
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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