Boron tribromide → HCID 135617183, compound

HRID 568508Notes

Reaction equation

HRID 568508 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:13]2[S:14][CH:15]=[CH:16][C:12]=2[O:11][N:10]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:13]2[S:14][CH:15]=[CH:16][C:12]=2[O:11][N:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 14097220HCID 14097220, compound

Product 1

HCID 135617183HCID 135617183, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 23 g of 3-(2-methoxyphenyl)thieno[2,3-d]isoxazole in 450 ml of dichloromethane was added a boron tribromide solution in dichloromethane (150 ml, 1 M solution) over one hour. The reaction mixture was stirred for an additional one hour at room temperature and then poured over 600 ml of ice water. A precipitate was filtered off and washed with 50% ether/ethyl acetate. The aqueous phase was also extracted with 50% ether/ethyl acetate and the combined solvent solution was washed with water and dried over anhydrous magnesium sulfate. Evaporation of the solvent solution left 17 g of a solid which was passed through a silica gel column packed in hexane and eluted with 50% ether/hexane. The resultant solid was recrystallized from ether/hexane to give 15 g of a solid, m.p. 121°-123 C.

Workup

  1. filtrationA precipitate was filtered off
  2. washwashed with 50% ether/ethyl acetate
  3. extractionThe aqueous phase was also extracted with 50% ether/ethyl acetate
  4. washthe combined solvent solution was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customEvaporation of the solvent solution
  7. waitleft 17 g of a solid which
  8. washeluted with 50% ether/hexane
  9. customThe resultant solid was recrystallized from ether/hexane

Sources & evidence

ORD record
ord-54acd3dd7d0a42ca8162c155833b0386
Source dataset
uspto-grants-1988_03
Patent number
US04728651

Reaction notes

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