Pyridine → 1-(2,6-Dichloro-3-fluorophenyl)ethyl acetate

HRID 1169699Notes

Reaction equation

HRID 1169699 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].N1C=CC=CC=1.[Cl:14][C:15]1[C:20]([F:21])=[CH:19][CH:18]=[C:17]([Cl:22])[C:16]=1C(O)C>C(Cl)Cl>[C:5]([O:4][CH:1]([C:16]1[C:17]([Cl:22])=[CH:18][CH:19]=[C:20]([F:21])[C:15]=1[Cl:14])[CH3:2])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 167700681-(2,6-Dichloro-3-fluorophenyl)ethan-1-ol

Product 1

HCID 166559501-(2,6-Dichloro-3-fluorophenyl)ethyl acetateYield 85.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (1.42 mL, 15 mmol) and pyridine (1.7 mL, 21 mmol) were added sequentially to a solution of compound A1 (2.2 g, 10.5 mmol) in 20 mL of CH2Cl2. The reaction mixture was stirred at room temperature for 12 h and then evaporated to give a yellowish oil residue. The residue was purified by flash chromatography (eluting with 7→9% EtOAc in hexanes) to give compound A2 as a colorless oil (2.26 g; 9.0 mmol; 85.6% yield); 1H NMR (400 MHz, chloroform-D) δ ppm 1.88 (d, J=6.82 Hz, 3 H) 2.31 (s, 3H) 6.62 (q, J=6.82 Hz, 1H) 7.25 (t, J=8.46 Hz, 1H) 7.49 (dd, J=8.84, 5.05 Hz, 1H).

Workup

  1. customevaporated
  2. customto give a yellowish oil residue
  3. customThe residue was purified by flash chromatography (eluting with 7→9% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3b153b40b66541acb8a5c48a3d5b12d6
Source dataset
uspto-grants-2010_11
Patent number
US07825137B2

Reaction notes

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