Water → 4-(5-Bromo-2,1-benzisoxazol-3-yl)phenyl methyl ether

HRID 235234Notes

Reaction equation

HRID 235234 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]#N)=[CH:7][CH:6]=1.[Br:14][C:15]1[CH:20]=C[C:18]([N+:21]([O-])=[O:22])=[CH:17][CH:16]=1.O>CO.O1CCCC1>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[O:22][N:21]=[C:18]3[CH:17]=[CH:16][C:15]([Br:14])=[CH:20][C:12]=23)=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 114661-Bromo-4-nitrobenzeneHCID 14797Potassium HydroxideHCID 66031Benzeneacetonitrile, 4-methoxy-

Product 1

HCID 3477664-(5-Bromo-2,1-benzisoxazol-3-yl)phenyl methyl ether

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 148 g of potassium hydroxide in 300 ml of anhydrous methanol at 0° C. was added 21.3 g (0.145 mole) of 4-methoxy phenylacetonitrile. The mixture was stirred at 0° C. for 10 min. and then a solution of 25.4 g (0.126 mol) of p-bromo nitrobenzene in 300 ml of tetrahydrofuran and methanol (1:2) was slowly added over a period of 1 h. The deep purple mixture was continuously stirred and maintained at 0°-5° C. during addition. The temperature was then raised to 55° C. using a hot water bath and reaction mixture was stirred for another 3 h. On cooling, the reaction mixture was poured into 1500 ml of water, and the brown precipitate was separated by suction filtration. The product was washed twice with water followed by cold methanol. The yellow solid so obtained was recrystallized twice from methanol to give needle like light yellow crystals. Yield 19.5 g (51%). mp 137.1° C. Anal. calcd. for C14H10NO2Br: c, 55.29; H, 3.31; N, 4.61. Found: C, 54.99; H, 3.14; N, 4.62.

Workup

  1. stirringThe deep purple mixture was continuously stirred
  2. temperaturemaintained at 0°-5° C. during addition
  3. temperatureThe temperature was then raised to 55° C.
  4. customreaction mixture
  5. stirringwas stirred for another 3 h
  6. temperatureOn cooling
  7. customthe brown precipitate was separated by suction filtration
  8. washThe product was washed twice with water
  9. customThe yellow solid so obtained
  10. customwas recrystallized twice from methanol
  11. customto give needle like light yellow crystals

Sources & evidence

ORD record
ord-b4e5c778010e43dcbef74792f5ad0687
Source dataset
uspto-grants-1997_01
Patent number
US05597890

Reaction notes

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