Hydrogen Bromide → HCID 178515935, compound

HRID 384313Notes

Reaction equation

HRID 384313 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[NH:19][N:18]=[N:17][N:16]=2)[CH:10]=1.Br>C(O)(=O)C>[NH:19]1[C:15]([C:11]2[CH:10]=[C:9]([C:4]3[C:3]([OH:2])=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:14]=[CH:13][CH:12]=2)=[N:16][N:17]=[N:18]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 178489286HCID 178489286, compound

Product 1

HCID 178515935HCID 178515935, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-(2′-Methoxy-biphenyl-3-yl)-1H-tetrazole 8c (15.5 g, 61.5 mol) was dissolved in 195 mL of acetic acid followed by addition of 195 mL of hydrobromic acid under argon atmosphere. The reaction mixture was heated to reflux for 5 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was cooled to room temperature overnight. The mixture was filtered and the filter cake was dissolved in 500 mL of ethyl acetate. The mixture was washed with water (500 mL×2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized from 100 mL of ethyl acetate to obtain the title compound 3′-(1H-tetrazol-5-yl)-biphenyl-2-ol 8d (12 g, yield 82.8%) as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 hours
  3. filtrationThe mixture was filtered
  4. dissolutionthe filter cake was dissolved in 500 mL of ethyl acetate
  5. washThe mixture was washed with water (500 mL×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from 100 mL of ethyl acetate

Sources & evidence

ORD record
ord-3ec8910c2d3b43c2abc5ce6e02e37613
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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