Allyl bromide → 2-{4-[(Prop-2-en-1-yl)oxy]phenyl}-1,3-benzoxazole

HRID 1618058Notes

Reaction equation

HRID 1618058 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[CH2:17](Br)[CH:18]=[CH2:19].C([O-])([O-])=O.[Na+].[Na+]>CN1CCCC1=O.C(OC(=O)C)C>[CH2:19]([O:16][C:13]1[CH:14]=[CH:15][C:10]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)=[CH:11][CH:12]=1)[CH:18]=[CH2:17]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 27855874-(Benzo[d]oxazol-2-yl)phenol

Product 1

HCID 135703742-{4-[(Prop-2-en-1-yl)oxy]phenyl}-1,3-benzoxazoleYield 86.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A 500 ml round bottom flask, equipped with a reflux condenser and an oil bath with a magnetic stirrer was charged with 13.94 g of the above 4-(2-benzoxazolyl)-phenol, 9.7 g of allyl bromide and 17.5 g of anhydrous Na2CO3 in 300 ml of 1-methyl-2-pyrrolidone. A trace of KJ was added. After 5 h hour at 110° C. no starting material could be observed on tlc. The reaction mixture was diluted with ethylacetate and washed with 1n NaOH, water and NaCl solution, dried with Na2SO4, concentrated and recrystallised from hexene to yield 14.3 g (86%) of 2-(4-prop-2-enyloxy-phenyl)-benzoxazole. M.p. 95-96° C., UV (ethanol) 308 nm (26′184).

Workup

  1. customA 500 ml round bottom flask, equipped with a reflux condenser and an oil bath with a magnetic stirrer
  2. additionA trace of KJ was added
  3. washwashed with 1n NaOH, water and NaCl solution
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. customrecrystallised from hexene

Sources & evidence

ORD record
ord-6af6f8f905844d9ebe96cd8205834f44
Source dataset
uspto-grants-2014_07
Patent number
US08765967B2

Reaction notes

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