Carbon tetrabromide → 4-[2-(4-Bromomethyl-phenoxy)-ethyl]-5-methyl-2-phenyl-oxazole

HRID 644010Notes

Reaction equation

HRID 644010 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[CH3:25][C:26]1[O:30][C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N:28][C:27]=1[CH2:37][CH2:38][O:39][C:40]1[CH:45]=[CH:44][C:43](CO)=[CH:42][CH:41]=1>C(Cl)Cl>[Br:24][CH2:20][C:43]1[CH:44]=[CH:45][C:40]([O:39][CH2:38][CH2:37][C:27]2[N:28]=[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:30][C:26]=2[CH3:25])=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 118338284-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl alcohol

Product 1

HCID 685793194-[2-(4-Bromomethyl-phenoxy)-ethyl]-5-methyl-2-phenyl-oxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (2.54 g, 9.7 mmol) is added to a solution of carbon tetrabromide (3.22 g, 9.7 mmol) and the title B compound, {4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-methanol (2.0 g, 6.46 mmol) in DCM (24 mL) at RT. The mixture is stirred overnight and then concentrated under vacuum. The residue is chromatographed on silica gel using 15% EtOAc in hexane as the eluent to provide 4-[2-(4-bromomethyl-phenoxy)-ethyl]-5-methyl-2-phenyl-oxazole as a white solid.

Workup

  1. customat RT
  2. concentrationconcentrated under vacuum
  3. customThe residue is chromatographed on silica gel using 15% EtOAc in hexane as the eluent

Sources & evidence

ORD record
ord-5cc5ddff80e8440bad0794267d7f33a6
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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