Phosphorus tribromide → 5-(Bromomethyl)-4-methyl-2-phenyloxazole

HRID 2120163Notes

Reaction equation

HRID 2120163 reaction equation
P(Br)(Br)[Br:2].[CH3:5][C:6]1[N:7]=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:9][C:10]=1[CH2:11]O>CCOCC.C(Cl)Cl>[Br:2][CH2:11][C:10]1[O:9][C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:7][C:6]=1[CH3:5]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 23438974(4-Methyl-2-phenyl-1,3-oxazol-5-yl)methanol

Product 1

HCID 234390045-(Bromomethyl)-4-methyl-2-phenyloxazole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

80 mL (0.67 mmol) of PBr3 is added slowly to a solution of 104 mg (0.57 mmol) of (4-methyl-2-phenyl-oxazol-5-yl)-methanol in 0.5 mL of Et2O and 1.5 mL of CH2Cl2 at 0° C. The cooling bath is removed, and the reaction mixture is stirred for 4 h. The reaction mixture is then partitioned between saturated aqueous NaHCO3 solution and Et2O. The organic phase is separated and washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to produce 5-bromomethyl-4-methyl-2-phenyl-oxazole as a solid; 1H NMR (250 MHz, CDCl3) δ7.90-7.99 (m, 2H), 7.32-7.40 (m, 3H), 4.50 (s, 2H), 2.16 (s, 3H).

Workup

  1. customThe cooling bath is removed
  2. customThe reaction mixture is then partitioned between saturated aqueous NaHCO3 solution and Et2O
  3. customThe organic phase is separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13b71330ccda4d47a8f0c4453f84fbf0
Source dataset
uspto-grants-2004_02
Patent number
US06689801B2

Reaction notes

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