Pyridiniumtribromide → HCID 67955772, compound

HRID 872274Notes

Reaction equation

HRID 872274 reaction equation
[CH:1]1([CH2:5][N:6]2[C:10]3[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=3[N:8]=[N:7]2)[CH2:4][CH2:3][CH2:2]1.[Br-:16].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:16][C:14]1[C:9]2[N:8]=[N:7][N:6]([CH2:5][CH:1]3[CH2:2][CH2:3][CH2:4]3)[C:10]=2[CH:11]=[CH:12][C:13]=1[OH:15]

Participants

4

Reactant 2

HCID 21124087PyridiniumtribromideHCID 67956040HCID 67956040, compound

Product 1

HCID 67955772HCID 67955772, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1-(cyclobutylmethyl)-1H-benzotriazol-5-ol (3-4, 280 mg, 1.38 mmol, 1 equiv) and pyridinium tribromide (551 mg, 1.72 mmol, 1.25 equiv) in chloroform (20 mL) was stirred at 23° C. for 4 h. The mixture was concentrated and the residue partitioned between saturated aqueous sodium bicarbonate solution (100 mL) and ethyl acetate (2×50 mL). The combined organic layers were dried over sodium sulfate and concentrated to give 4-bromo-1-(cyclobutylmethyl)-1H-benzotriazol-5-ol (3-5) as an orange solid. 1H NMR (300 MHz, CDCl3) δ 7.38 (d, 1H, J=8.9 Hz), 7.25 (d, 1H, J=8.9 Hz), 5.92 (br s, 1H), 4.60 (d, 2H, J=7.0 Hz), 2.96 (p, 1H, J=7.6 Hz), 2.06 (m, 2H), 1.89 (m, 4H) ppm. LRMS m/z (M+H) 283.9 found, 284.0 required.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue partitioned between saturated aqueous sodium bicarbonate solution (100 mL) and ethyl acetate (2×50 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8b52f1819e7f4617b069eed33bcf8ccd
Source dataset
uspto-grants-2015_03
Patent number
US08975286B2

Reaction notes

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