Pyridine → HCID 59838040, compound

HRID 1438132Notes

Reaction equation

HRID 1438132 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.N1C=CC=CC=1.[C:17](Cl)(=[O:19])[CH3:18]>C(Cl)Cl.CCOC(C)=O>[C:17]([O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[O:9][CH3:10])(=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 27373684-Fluoro-2-methoxyphenol

Product 1

HCID 59838040HCID 59838040, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-fluoro-2-methoxyphenol (569 mg, 4.0 mmol) and pyridine (0.56 mL, 7.0 mmol) in CH2Cl2 (8.0 mL) at 0° C. was added acetyl chloride (0.33 mL, 4.6 mmol). The mixture was stirred at rt for 2.0 h and then diluted with EtOAc and washed with 4.0 N HCl. The organic layer was washed with brine and dried over Na2SO4. After evaporation of the solvent, 64A (680 mg, 92% yield) was obtained as a solid used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 2.29 (s, 3H) 3.79 (s, 3H) 6.62 (m, 1H) 6.68 (dd, J=10.33, 2.86 Hz, 1H) 6.95 (dd, J=8.79, 5.71 Hz, 1H).

Workup

  1. washwashed with 4.0 N HCl
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-3632d47d045a43768679364f0b37390c
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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