Triethylamine → 3-(4-chloro-3-nitrobenzylidene)-3H-isobenzofuran-1-one

HRID 459775

Reaction equation

HRID 459775 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4](P(=O)(OC)OC)[O:3]1.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][C:19]=1[N+:26]([O-:28])=[O:27].C(N(CC)CC)C>O1CCCC1>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2](=[O:1])[O:3]2)=[CH:20][C:19]=1[N+:26]([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 855054-Chloro-3-nitrobenzaldehydeHCID 11118213Dimethyl (3-oxo-1,3-dihydro-2-benzofuran-1-yl)phosphonate

Product 1

HCID 686228163-(4-chloro-3-nitrobenzylidene)-3H-isobenzofuran-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
15 °C

Procedure

A stirred solution of dimethyl 3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonate (4.84 g, 0.02 mol; prepared in a manner similar to that described in Example 23) and 4-chloro-3-nitrobenzaldehyde (3.71 g, 0.02 mol) in tetrahydrofuran (30 ml) was cooled to 15° C. and a solution of triethylamine (2.02 g, 0.02 mol) in tetrahydrofuran (3 ml) was added dropwise at <25° C. The mixture was stirred at ambient temperature for 1 hour, allowed to stand at this temperature for a further 16 hours and the resulting solid was collected by filtration. The filtrate was concentrated in vacuo, the residue was triturated with water (5 ml) and the resulting solid was collected by filtration. The two crops of solid were combined and suspended in water (30 ml). The mixture was stirred at ambient temperature for 30 minutes and the resulting solid was collected by filtration and dried in vacuo for 24 hours to give crude 3-(4-chloro-3-nitrobenzylidene)-3H-isobenzofuran-1-one as a pale yellow solid, m.pt. 198–204° C., still slightly wet with water, which was used directly in the next stage.

Workup

  1. customprepared in a manner similar to
  2. waitto stand at this temperature for a further 16 hours
  3. filtrationthe resulting solid was collected by filtration
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was triturated with water (5 ml)
  6. filtrationthe resulting solid was collected by filtration
  7. stirringThe mixture was stirred at ambient temperature for 30 minutes
  8. filtrationthe resulting solid was collected by filtration
  9. customdried in vacuo for 24 hours

Sources & evidence

ORD record
ord-eef7148da5474d7cb8dcb63a22b909da
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Linked notes

Loading…