1-Bromo-2-Chloroethane → 2-[4-[[4-(2-Chloroethoxy)phenyl]methyl]phenyl]oxazole

HRID 16508

Reaction equation

HRID 16508 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.[Cl:20][CH2:21][CH2:22]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.O>[Cl:20][CH2:21][CH2:22][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][C:9]2[CH:8]=[CH:7][C:6]([C:2]3[O:1][CH:5]=[CH:4][N:3]=3)=[CH:11][CH:10]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 10796Cesium carbonateHCID 684892774-[[4-(2-Oxazolyl)phenyl]methyl]phenol

Product 1

HCID 684847252-[4-[[4-(2-Chloroethoxy)phenyl]methyl]phenyl]oxazoleYield 98.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 4-[[4-(2-oxazol yl)phenyl]methyl]phenol (2.2 g, 8.75 mmol) and 2-chloroethylbromide (10 g, 70 mmol) in acetonitrile as stirred as cesium carbonate (22.8 g, 70 mmol) was added. The reaction was heated at reflux for 3 days. The reaction was diluted with water. The product, 2-[4-[[4-(2-chloroethoxy)phenyl]methyl]phenyl]oxazole (2.7 g), was isolated by filtration, 1H NMR (400 MHz, CDCl3) δ 7.97 (d, 2H), 7.68 (s, 1H), 7.35 (m, 2H), 7.21 (s, 1H), 7.13 (d, 2H), 6.82 (d, 2H), 4.22 (t, 2H), 3.96 (s, 2H), 3.79 (t, 2H).

Workup

  1. additionwas added
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 3 days

Sources & evidence

ORD record
ord-5bfd759ded6f484e80cd884eb5f0c84e
Source dataset
uspto-grants-2010_06
Patent number
US07737145B2

Linked notes

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