Bromine → HCID 58280022, compound

HRID 63279Notes

Reaction equation

HRID 63279 reaction equation
[CH3:1][C:2]([C:5]1[N:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[Br:12]Br>N1C=CC=CC=1.[Cl-].[Na+].O>[Br:12][C:9]1[C:8]([OH:11])=[CH:7][CH:6]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[N:10]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 229582676-Tert-butylpyridin-3-ol

Product 1

HCID 58280022HCID 58280022, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of 6-(1,1-dimethylethyl)-3-pyridinol, (3.8 g) in pyridine (150 ml) was added bromine (1.29 ml), diluted in pyridine, dropwise at 20 C. The reaction mixture was allowed to stir at 25-30 C. for 1 h. The reaction had gone to completion by tlc. It was poured into brine and extracted with ethyl acetate. The organics were dried over sodium sulphate and concentrated under reduced pressure. The crude material was subjected to flash chromatography using a 0-5% gradient of ethyl acetate in hexane to give the title compound, 2.9 g

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organics were dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d8a71c3e83c472c8a2ca3ad834ef1bb
Source dataset
uspto-grants-2016_09
Patent number
US09447074B2

Reaction notes

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