Carbon tetrabromide → HCID 21866849, compound

HRID 857216Notes

Reaction equation

HRID 857216 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][CH2:15][CH2:16][CH2:17]O.C(Br)(Br)(Br)[Br:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOCC>[Br:20][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:3]1[N:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:6][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21866910HCID 21866910, compound

Product 1

HCID 21866849HCID 21866849, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5-(5-Methyl-2-phenyloxazol-4-yl)-1-pentanol (2.9 g) was dissolved in 62 ml of dry ether, and 8.4 g of carbon tetrabromide was added. To the mixture was added gradually 6.6 g of triphenylphosphine under ice-cooling. The mixture was then stirred for 2.5 hours at room temperature, filtrated to remove insolubles and the filtrate was concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=10:1) to provide 2.61 g of the objective compound as yellowish oil.

Workup

  1. temperaturecooling
  2. filtrationfiltrated
  3. customto remove insolubles
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=10:1)

Sources & evidence

ORD record
ord-df5725e8cd584fe4b0455dbbe6aca4d4
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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