Pyridine → HCID 54503630, compound

HRID 1913308Notes

Reaction equation

HRID 1913308 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].N1C=CC=CC=1.[C:16](Cl)(=[O:18])[CH3:17]>ClCCl>[C:16]([O:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=1[F:1])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 808792,3-Difluorophenol

Product 1

HCID 54503630HCID 54503630, compoundYield 103.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2,3-difluorophenol (30.0 g, 231 mmol) and pyridine (18.6 mL, 231 mmol) in dichloromethane (230 mL) at 0° C. was carefully added acetyl chloride (16.4 mL, 231 mmol). The reaction was allowed to warm to ambient temperature and stirred for 16 h. The reaction mixture was then diluted with dichloromethane (100 mL), washed with 1N aqueous hydrochloric acid (2×50 mL) and brine (75 mL), and concentrated to produce 41.0 g (100%) of the title compound. MS (DCI/NH3) m/z 190 (M+NH4)+.

Workup

  1. customat 0° C.
  2. washwashed with 1N aqueous hydrochloric acid (2×50 mL) and brine (75 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-86c98385a17e4abc99d614da46c61b3c
Source dataset
uspto-grants-2013_12
Patent number
US08609692B2

Reaction notes

Loading…