Ethanol → 6-Chloro-5-fluoropyridine-3-carbaldehyde

HRID 536166

Reaction equation

HRID 536166 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9](Br)Br)=[CH:4][N:3]=1.C([OH:14])C>[N+]([O-])([O-])=O.[Ag+].O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH:9]=[O:14])=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 702EthanolHCID 866970262-Chloro-5-(dibromomethyl)-3-fluoropyridine

Product 1

HCID 216981946-Chloro-5-fluoropyridine-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Procedure

A suspension 2-chloro-5-(dibromomethyl)-3-fluoropyridine (2.3 g, 7.58 mmol), silver nitrate (5.15 g, 30.3 mmol) in a mixed solvents of ethanol (10 mL) and water (10 mL) was stirred for 1 h at 100° C., then filtrated, and concentrated. The residue was dissolved in ethyl acetate, washed with water and brine, dried over sodium sulfate, concentrated. Purification via ISCO system afforded the title product (1.0 g) as a pale solid. LC-MS (ESI): m/z 159 [M+H]+; 2.01 min (ret time).

Workup

  1. filtrationfiltrated
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification via ISCO system

Sources & evidence

ORD record
ord-dc20eafd28f64893a4550c669ed52d48
Source dataset
uspto-grants-2014_10
Patent number
US08859573B2

Linked notes

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