Methanol → HCID 136395593, compound

HRID 2378068Notes

Reaction equation

HRID 2378068 reaction equation
B(Br)(Br)Br.CO.[CH3:7][O:8][C:9]([C:11]1([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=3)[C:15]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:13][CH2:12]1)=[O:10]>ClCCl>[CH3:7][O:8][C:9]([C:11]1([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[C:15]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:12][CH2:13]1)=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 68957204HCID 68957204, compound

Product 1

HCID 136395593HCID 136395593, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution consisting of boron tribromide (114 mL of a 1 M solution in dichloromethane) and dichloromethane (100 mL) is cooled in an ice/salt/methanol bath to −10° C. and a solution consisting of 1-[3-(4-methoxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropanecarboxylic acid methyl ester (10 g) dichloromethane (150 mL) is added dropwise while the temperature is maintained at −10° C. over 1 hour. The reaction mixture is allowed to warm to 0° C. and stirred for 4 hours until all starting material is consumed. The solution is cooled to −10° C. and 5% sodium bicarbonate solution (250 mL) is added slowly by addition funnel while maintaining the temperature below 0° C. The reaction flask is removed from the cold bath and water added, the organic layer is separated, dried, and concentrated to give 1-[3-(4-hydroxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropanecarboxylic acid methyl ester (9.6 g.)

Workup

  1. additionis added dropwise while the temperature
  2. temperatureto warm to 0° C.
  3. customis consumed
  4. temperatureThe solution is cooled to −10° C.
  5. addition5% sodium bicarbonate solution (250 mL) is added slowly by addition funnel
  6. temperaturewhile maintaining the temperature below 0° C
  7. customThe reaction flask is removed from the cold bath and water
  8. additionadded
  9. customthe organic layer is separated
  10. customdried
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-acbe1aee58a94622b1051733e0ec9de9
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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