Boron tribromide → HCID 135617183, compound

HRID 622209Notes

Reaction equation

HRID 622209 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, 1M 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-e6971ed43eaf4c89991fdb6950b9778e
Source dataset
uspto-grants-1988_09
Patent number
US04769472

Reaction notes

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