Water → HCID 22090626, compound

HRID 1993718Notes

Reaction equation

HRID 1993718 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:15]2[C:11](=[CH:12][O:13][N:14]=2)[CH:10]=[CH:9][CH:8]=1.O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[N:14]1[O:13][CH:12]=[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([OH:6])[C:15]=12

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 118296117-Methoxy-2,1-benzisoxazole

Product 1

HCID 22090626HCID 22090626, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

18.5 ml of a 1M solution of boron tribromide in dichloromethane are added to a solution of 1.38 g (9.25 mM) of 7-methoxy-2,1-benzisoxazole in 50 ml of dichloromethane cooled to −78° C., and the mixture is then stirred at ambient temperature overnight. The reaction medium is poured into water and the mixture is brought to pH=7-8 by adding a solution of sodium carbonate, and then extracted with dichloromethane. The organic phase is dried over magnesium sulfate and concentrated under vacuum. The crude product obtained is purified by silica gel chromatography, elution being carried out with a methylcyclohexane/ethyl acetate mixture (gradient of 100/0 to 50/50; v/v). The expected product is obtained in the form of a yellow solid with a yield of 10%.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe crude product obtained
  5. customis purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-579ced030d5344a1ab70608b0c3082f3
Source dataset
uspto-grants-2010_01
Patent number
US07652032B2

Reaction notes

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