Pyridine → HCID 54503630, compound

HRID 536453Notes

Reaction equation

HRID 536453 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 hours. 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-ce7008cdfd754b96bcd528adcc505315
Source dataset
uspto-grants-2014_10
Patent number
US08859584B2

Reaction notes

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