Carbon tetrabromide → 4-(2-Bromoethyl)-5-methyl-2-phenyloxazole

HRID 1729054Notes

Reaction equation

HRID 1729054 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.C(Br)(Br)(Br)[Br:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOCC>[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][Br:17]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanol

Product 1

HCID 156164424-(2-Bromoethyl)-5-methyl-2-phenyloxazoleYield 60.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

2-(5-Methyl-2-phenyl-4-oxazolyl)ethanol (0.203 g, 1.0 mmol; European patentapplication 177353) and CBr4 (0.662 g, 2.0 mmol) were dissolved in 10 mL of ether and cooled to 0° C. Triphenylphosphine (0.524 g, 2.0 mmol) was added and the mixture stirred for 3 hours at room temperature. The mixture was filtered, the filtrate was stripped of solvent and the residue filtered through a plug of silica gel using CHCl3 as eluant to yield 0.16 g of present title product as a white solid; mp 59°-61° C.; tlc Rf 0.22 (CHCl3).

Workup

  1. filtrationThe mixture was filtered
  2. filtrationthe residue filtered through a plug of silica gel

Sources & evidence

ORD record
ord-93e00c242297436680507cb2d858a432
Source dataset
uspto-grants-1994_07
Patent number
US05330998

Reaction notes

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