Phosphorus oxychloride → 3-Chlorobenzofuran-2-carboxaldehyde

HRID 1362365

Reaction equation

HRID 1362365 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]([CH2:9][O:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](O)=O)(O)=[O:7]>CN(C=O)C>[Cl:3][C:13]1[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[O:10][C:9]=1[CH:6]=[O:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 69461Benzoic acid, 2-(carboxymethoxy)-

Product 1

HCID 47370203-Chlorobenzofuran-2-carboxaldehydeYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled solution of phosphorus oxychloride (19 mL, 209 mmol) in DMF (40 mL) is slowly added 2-carboxymethoxybenzoic acid (6.84 g, 35 mmol) in portions. The mixture is warmed to room temperature for 30 min and then heated to 90° C. overnight. The mixture is cooled to room temperature and poured carefully into ice water, extracted with ethyl acetate (3×50 mL), dried with sodium sulfate and concentrated in vacuo. Purification by column chromatography (silica, hexanes/ethyl acetate, 4:1) gave title compound (1.62 g, 26%) as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ 9.98 (s, 1H), 7.82-7.88 (m, 2H), 7.69-7.73 (m, 1H), 5.51-7.56 (m, 1H).

Workup

  1. temperatureheated to 90° C. overnight
  2. temperatureThe mixture is cooled to room temperature
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by column chromatography (silica, hexanes/ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-59e99151cb16412a9600ded35def9939
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Linked notes

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