Boron tribromide → HCID 67363990, compound

HRID 1771373Notes

Reaction equation

HRID 1771373 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[N:15]=[N:14][C:13]([NH2:16])=[N:12][C:11]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=[C:6]([O:8]C)[CH:7]=1.B(Br)(Br)Br>O>[NH2:16][C:13]1[N:14]=[N:15][C:10]([C:4]2[CH:5]=[C:6]([OH:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)=[C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 53354727HCID 53354727, compound

Product 1

HCID 67363990HCID 67363990, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(3-Amino-5-phenyl-1,2,4-triazin-6-yl)-5-chlorophenol (890 mg, 85%) was prepared by demethylation of 6-(3-chloro-5-methoxyphenyl)-5-phenyl-1,2,4-triazin-3-amine (1.2 g, 3.84 mmol; vide supra) with BBr3 (5 mL) at −70° C. for 2 hours and then for a further 16 hours at RT. The resulting mixture was then poured into water (25 mL) and extracted with DCM (3×30 mL). The combined organic extracts were then dried over Na2SO4 and concentrated under vacuum. The crude compound was purified by gradient flash chromatography, eluting with 30% ethyl acetate in hexane to afford the target compound.

Workup

  1. extractionextracted with DCM (3×30 mL)
  2. dry with materialThe combined organic extracts were then dried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customThe crude compound was purified by gradient flash chromatography
  5. washeluting with 30% ethyl acetate in hexane
  6. customto afford the target compound

Sources & evidence

ORD record
ord-cd6871dcbfde4df2b1c0129ff973bd47
Source dataset
uspto-grants-2016_02
Patent number
US09249130B2

Reaction notes

Loading…