Hydrogen Bromide → 3-Bromo-6-nitrofuro[3,2-c]pyridin-7-ol

HRID 912012Notes

Reaction equation

HRID 912012 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([N+:23]([O-:25])=[O:24])=[C:10]([O:11]C(C3C(Cl)=CC=C(F)C=3Cl)C)[C:5]=2[O:4][CH:3]=1.Br>O>[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([N+:23]([O-:25])=[O:24])=[C:10]([OH:11])[C:5]=2[O:4][CH:3]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 578123503-Bromo-7-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-6-nitrofuro[3,2-c]pyridine2×

Product 1

HCID 578123753-Bromo-6-nitrofuro[3,2-c]pyridin-7-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-Bromo-7-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-6-nitrofuro[3,2-c]pyridine (Intermediate 9a) (1.90 g, 0.00422 mol) in 48% aq. hydrogen bromide (100 mL, 2.0 mol) was stirred at 60° C. overnight. The reaction mixture was cooled down to rt. The reaction solution was diluted with H2O (100 mL) and extracted with DCM (5×50 mL). The DCM solution was dried over Na2SO4 and concentrated under vacuum. The resulting solid was triturated with DCM/hexanes to give the title compound. MS (ES+): m/z 258.85/260.89 [MH+]. HPLC: tR=2.81 min (ZQ3, polar—5 min). 1H NMR (400 MHz, CD3OD): δ=8.28 (s, 1H) 8.32 (s, 1H).

Workup

  1. extractionextracted with DCM (5×50 mL)
  2. dry with materialThe DCM solution was dried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customThe resulting solid was triturated with DCM/hexanes

Sources & evidence

ORD record
ord-6a49f978314e4b408e92e8b7014d817e
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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