Carbon tetrabromide → 4-(3-Bromo-propyl)-5-methyl-2-phenyl-oxazole

HRID 2121695Notes

Reaction equation

HRID 2121695 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]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:37]>ClCCl>[Br:37][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 120932653-(5-Methyl-2-phenyl-oxazol-4-yl)-propan-1-ol

Product 1

HCID 120932664-(3-Bromo-propyl)-5-methyl-2-phenyl-oxazoleYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Alcohol 1-4 (3 g, 13.8 mmol) was dissolved in dichloromethane (200 mL) and cooled to 0° C. under N2 atmosphere. Triphenylphosphine (4.35 g, 16.6 mmol) was added followed by CBr4 (5.5 g, 16.6 mol) in small portions. Reaction temperature was allowed to equilibrate to 23° C. over 8 hours. 20 g of SiO2 gel was added and solvent removed in vacuo. The dried silica gel was placed in a filter and washed with 10% EtOAc/Hexanes. The filtrate was reduced to minimum volume and chromatographed with 5-10% EtOAc/Hexanes to give 3.5 g of the product 1-5 as a clear oil (90% yield). M+1=280.0/282.1.

Workup

  1. customReaction temperature
  2. customsolvent removed in vacuo
  3. filtrationa filter
  4. washwashed with 10% EtOAc/Hexanes
  5. customchromatographed with 5-10% EtOAc/Hexanes

Sources & evidence

ORD record
ord-5c38f4a116f74b1d97f94363f38ea3cc
Source dataset
uspto-grants-2004_02
Patent number
US06696474B2

Reaction notes

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