Acetic Anhydride → HCID 22607358, compound

HRID 2307752Notes

Reaction equation

HRID 2307752 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([OH:8])[CH:7]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10].C(N(CC)CC)C>C1COCC1.C(OCC)C>[C:9]([O:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Br:1])[CH:7]=1)(=[O:11])[CH3:10]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 5995293-Bromo-5-hydroxypyridine

Product 1

HCID 22607358HCID 22607358, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-bromo-5-hydroxypyridine (9.00 g, 51.7 mmol), acetic anhydride (6.0 mL) and triethylamine (12.0 mL) in THF (50 mL) was heated to reflux overnight, cooled to room temperature, diluted with diethyl ether, washed with water, 5% NaHCO3, water, and brine, dried (MgSO4), filtered, and concentrated to provide the desired product (9.37 g, 84%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. washwashed with water, 5% NaHCO3, water, and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e227cd3dc9e74572b964856f71ce8e50
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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