Boron tribromide → 4-((5-Bromo-1,3,4-thiadiazol-2-yl)oxy)phenol

HRID 404887Notes

Reaction equation

HRID 404887 reaction equation
[Br:1][C:2]1[S:3][C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][CH:9]=2)=[N:5][N:6]=1.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[S:3][C:4]([O:7][C:8]2[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=2)=[N:5][N:6]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 646250762-Bromo-5-(4-methoxyphenoxy)-1,3,4-thiadiazole

Product 1

HCID 665451074-((5-Bromo-1,3,4-thiadiazol-2-yl)oxy)phenolYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of Example 24A (1.63 g, 5.67 mmol) in CH2Cl2 (75 mL) was cooled to −78° C. and the resulting suspension was treated with BBr3 (22.67 mmol, 2.14 mL) drop wise over 2 minutes. The reaction was stirred at 25° C. for 2 hours and was poured into a 200 mL ice/water mixture. The resulting bilayer was stirred vigorously for 0.5 hours and a white precipitate formed. The solids were filtered, washed with water (1×20 mL) and dried in a vacuum oven to provide 1.35 g (87%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.79 (br. s, 1H) 7.27 (d, J=9.19 Hz, 2H) 6.84 (d, J=9.19 Hz, 2H); MS (DCI) m/z 275 (M+H)+.

Workup

  1. stirringThe resulting bilayer was stirred vigorously for 0.5 hours
  2. customa white precipitate formed
  3. filtrationThe solids were filtered
  4. washwashed with water (1×20 mL)
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-aa224e66aadc47b1b70c8b07ef7f5d88
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

Loading…