Hydrochloric Acid → HCID 22221088, compound

HRID 1794310Notes

Reaction equation

HRID 1794310 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[C:14](OCC)=[O:15])[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[CH2:14][OH:15])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22221304HCID 22221304, compound

Product 1

HCID 22221088HCID 22221088, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-(3-bromo-4-chlorophenyl)isoxazole-4-carboxylate (6.19 g) in tetrahydrofuran (100 ml) was gently added diisobutylaluminum hydride (1.0 M tetrahydrofuran solution, 40 ml) at 0° C. and the mixture was stirred at room temperature for 30 min. The reaction mixture was poured into dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give 5-(3-bromo-4-chlorophenyl)-4-isoxazolylmethanol (5.10 g, yield 94%) as a colorless oil. NMR (CDCl3) δ: 4.73 (2H, d, J=4.8 Hz), 7.59 (1H, d, J=8.4 Hz), 7.72 (1H, dd, J=2.2, 8.4 Hz), 8.10 (1H, d, J=2.2 Hz), 8.37 (1H, s).

Workup

  1. customat 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3bfb32147d374e11978f53b87fb04f94
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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