Boron tribromide → HCID 14424744, compound

HRID 1165481Notes

Reaction equation

HRID 1165481 reaction equation
C[O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]3[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=3)[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]3[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=3)[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 14424741HCID 14424741, compound

Product 1

HCID 14424744HCID 14424744, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The methyl 4-(4-methoxybenzothiazol-2-yl)benzoate (11.3 g) obtained in Example 3 (3) was dissolved in 200 ml of dichloromethane, and a solution of 9.5 g of boron tribromide in 80 ml of dichloromethane was added dropwise to the solution. The mixture was stirred at room temperature for 2.5 hours, then poured into 300 ml of ice water, extracted with chloroform three times, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (eluted with chloroform), and the solvent was evaporated under reduced pressure. The residue was washed with a small amount of chloroform, and recrystallized from ethyl acetate to give 3.6 g of methyl 4-(4-hydroxybenzothiazol-2-yl)benzoate. mp 215°-219.0° C.

Workup

  1. extractionextracted with chloroform three times
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. washThe residue was subjected to silica gel column chromatography (eluted with chloroform)
  5. customthe solvent was evaporated under reduced pressure
  6. washThe residue was washed with a small amount of chloroform
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-414e672dbecb491cbfa6b6f03ede7a2b
Source dataset
uspto-grants-1990_03
Patent number
US04910211

Reaction notes

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