Propargyl bromide → 5-(Bromomethyl)-3-phenylisoxazole

HRID 2248969Notes

Reaction equation

HRID 2248969 reaction equation
[CH2:1]([Br:4])[C:2]#[CH:3].[Na].[CH:6](=[N:13][OH:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>ClCCl>[Br:4][CH2:1][C:2]1[O:14][N:13]=[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 12143(Z)-Benzaldehyde oximeHCID 5360545Sodium

Product 1

HCID 27487965-(Bromomethyl)-3-phenylisoxazoleYield 55.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of propargyl bromide (1.51 ml, 20 mmol) in dichloromethane (15 ml) and aqueous sodium hyopchlorite (22.4 ml, 10%, 30 mmol) at 0° C. was added dropwise with stirring benzaldoxime (2.42 g, 20 mmol) in dichloromethane (15 ml). When addition was complete the ice bath was removed and the reaction stirred for a further 2 h. The organic layer was separated and the aqueous layer washed with dichloromethane (2×20 ml) then the combined organic layers dried (MgSO4). Solvent removal under reduced pressure gave a solid which was recrystallised from 40°-60° C. petroleum ether fraction to give the desired isoxazole (2.64 g, 11.1 mmol, 55%); mp 82°-3° C., δH (CDCl3) 4.40(2H, s, CH2 -Br), 6.50(1H, s, CH-4), 7.3-7.9(5H, m, C6H5).

Workup

  1. additionWhen addition
  2. customwas removed
  3. customThe organic layer was separated
  4. washthe aqueous layer washed with dichloromethane (2×20 ml)
  5. dry with materialthe combined organic layers dried (MgSO4)
  6. customSolvent removal under reduced pressure
  7. customgave a solid which
  8. customwas recrystallised from 40°-60° C. petroleum ether fraction

Sources & evidence

ORD record
ord-fda063322f4e4bbd9ca9740bede52f11
Source dataset
uspto-grants-1991_08
Patent number
US05041567

Reaction notes

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