Acetyl chloride → 5-Bromo-2-pyridinyl Acetate

HRID 907042Notes

Reaction equation

HRID 907042 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.C(N(CC)CC)C.[C:16](Cl)(=[O:18])[CH3:17]>C(OCC)C>[C:16]([O:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178515818HCID 178515818, compound

Product 1

HCID 234385765-Bromo-2-pyridinyl AcetateYield 52%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 0.5 g (2.87 mmol) of 5-bromo-2-pyridinol in 10 ml of ethyl ether is prepared and 1 ml (7.1 mmol) of triethylamine and then 1 ml (14 mmol) of acetyl chloride are added at ambient temperature. The mixture is stirred at ambient temperature for 24 hours and then the insoluble materials are removed by filtration. The filtrate is concentrated under reduced pressure and the crude product is purified by chromatography on silica gel, elution being carried out using a toluene/2-propanol mixture (9/1; v/v). The expected product is obtained in the form of a pale yellow powder with a yield of 52%.

Workup

  1. customis prepared
  2. customthe insoluble materials are removed by filtration
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customthe crude product is purified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-494fc5c5a5db4fb3a27b111fd16d8f74
Source dataset
uspto-grants-2011_09
Patent number
US08013010B2

Reaction notes

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