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Hydrochloric Acid → 3-(3,5-Dichloro-pyridin-4-ylmethylene)-6-difluoromethoxy-3H-isobenzofuran-1-one

HRID 2268898
Notes
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Reaction equation

HRID 2268898 reaction equation
[Br-].[F:2][CH:3]([F:34])[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH:10]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[O:9][C:8]2=[O:33].[Cl:35][C:36]1[CH:37]=[N:38][CH:39]=[C:40]([Cl:44])[C:41]=1[CH:42]=O.C(N(CC)CC)C.Cl>C(Cl)Cl>[Cl:35][C:36]1[CH:37]=[N:38][CH:39]=[C:40]([Cl:44])[C:41]=1[CH:42]=[C:10]1[C:11]2[C:7](=[CH:6][C:5]([O:4][CH:3]([F:2])[F:34])=[CH:13][CH:12]=2)[C:8](=[O:33])[O:9]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27629883,5-Dichloro-4-pyridinecarboxaldehydeHCID 18381616HCID 18381616, compound

Product 1

HCID 538635133-(3,5-Dichloro-pyridin-4-ylmethylene)-6-difluoromethoxy-3H-isobenzofuran-1-oneYield 191.5%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
4 °C

Procedure

A solution of (5-difluoromethoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-triphenyl-phosphonium bromide (11.4 g, 21 mmoles), prepared as described in example 96, in dry CH2Cl2 (110 ml), under N2, was added with 3,5-dichloro-4-formyl-pyridine (4.06 g, 23.1 mmoles). The mixture was cooled to 4° C. and added with triethylamine (3.8 ml, 27.3 mmoles) while keeping the temperature below 10° C. At the end of the addition the mixture was stirred at room temperature for 3 hours, then cooled and added with 5% HCl. The organic phase was washed with an aqueous NaCl solution, discoloured with charcoal, filtered over celite and dried to give 14.4 g of the title compound (stoichiometric yield; containing 1 equivalent of triphenylphosphine oxide).

Workup

  1. customthe temperature below 10° C
  2. additionAt the end of the addition the mixture
  3. temperaturecooled
  4. washThe organic phase was washed with an aqueous NaCl solution
  5. filtrationfiltered over celite
  6. customdried

Sources & evidence

ORD record
ord-0556a80c35ff406ea82564e8aa5201f2
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06329370B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes