Phenethyl bromide → HCID 6483409, compound

HRID 2227466Notes

Reaction equation

HRID 2227466 reaction equation
[CH3:1][S:2][C:3]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[O:5][N:4]=1.[C:17]1([CH2:23][CH2:24]Br)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:1][S:2][C:3]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:24][CH2:23][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)[O:5][N:4]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 135525222HCID 135525222, compound

Product 1

HCID 6483409HCID 6483409, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Equimolecular amounts of (III), 2-phenyl-ethyl bromide and K2CO3 were refluxed in acetone for 48 h. The mixture was concentrated to small volume and shaken with diethyl ether and water. The ether phase was washed with 2 M NaOH, then with water, evaporated to dryness and the residue was recrystallized from ethanol. The title product was obtained in an 80% yield (abbreviation ON-6), m.p. 93-940° C. (ethanol); IR (KBr) 2227 (CN) cm1; 1H NMR (CDCl3) (δ, ppm) 2.66 (s, 3H, SCH3); 3.14 (t, 2H, CH2—Ph); 4.26 (t, 2H, O—CH2); 7.30 (m, 5H, arom.); 6.99-8.00 (m, 4H, arom.).

Workup

  1. concentrationThe mixture was concentrated to small volume
  2. washThe ether phase was washed with 2 M NaOH
  3. customwith water, evaporated to dryness
  4. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-256d619071ed4830aebb4e85f484e208
Source dataset
uspto-grants-2002_07
Patent number
US06414004B1

Reaction notes

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