Hydrogen Bromide → 4-[2-(4-Bromomethyl-naphthalen-1-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole

HRID 479119Notes

Reaction equation

HRID 479119 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.[BrH:26].O1CC[CH2:30]OO1>C(Cl)Cl>[Br:26][CH2:30][C:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:6][C:2]=2[CH3:1])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 180034585-Methyl-4-[2-(naphthalen-1-yloxy)-ethyl]-2-phenyl-oxazoleHCID 19593658CID 19593658

Product 1

HCID 180035404-[2-(4-Bromomethyl-naphthalen-1-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.494 g of 5-Methyl-4-[2-(naphthalen-1-yloxy)-ethyl]-2-phenyl-oxazole (1.50 mmol) was dissolved under argon atmosphere in 6 ml of CH2Cl2 and cooled down to 0°. 0.455 ml of 62% aq. HBr was added, followed by 58 mg of trioxane (0.644 mmol, 1.29 eq.). After 2 h, additional 0.455 ml of 62% aq. HBr was added and stirring continued for totally 5 h under strict temperature control. The reaction mixture was then diluted with CH2Cl2, washed with sat. NaHCO3-sol., the aqueous layer extracted once more with CH2Cl2, the combined organic phases dried over sodium sulfate and evaporated to dryness. This left 0.70 g of the crude title compound which was used as such for the next step. The product is quite unstable and can not be purified by column chromatography on SiO2; it also decomposes readily on TLC-plates.

Workup

  1. temperaturecooled down to 0°
  2. waitcontinued for totally 5 h under strict temperature control
  3. washwashed with sat. NaHCO3-sol
  4. extraction, the aqueous layer extracted once more with CH2Cl2
  5. dry with materialthe combined organic phases dried over sodium sulfate
  6. customevaporated to dryness
  7. customcan not be purified by column chromatography on SiO2

Sources & evidence

ORD record
ord-c3f73c257fd44c3282d5704abe49f3a4
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

Loading…