Hydrochloric Acid → HCID 3069818, compound

HRID 1606558Notes

Reaction equation

HRID 1606558 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[C:12]1(=[O:18])[O:17][C:15](=[O:16])[CH:14]=[CH:13]1.Cl>CCOCC.[Cl-].[Cl-].[Zn+2]>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([C:12]([CH:13]=[CH:14][C:15]([OH:17])=[O:16])=[O:18])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7923Maleic AnhydrideHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-

Product 1

HCID 3069818HCID 3069818, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent3×

Procedure

Freshly fused ZnCl2 (82 g, 0.6 mole) was dissolved in dry Et2O (400 ml) and added dropwise to the Grignard reagent prepared from 4-bromobenzotrifluoride (112.5g, 0.5 mole) and Mg(12.2 g, 0.5 g-atom) in Et2O (600 ml). Maleic anhydride (44 g, 0.45 mole) in Et2O (400 ml) was added over 30 minutes with stirring at reflux. After 2 hours, the mixture was cooled and acidified to pH 2 with 10% HCl. The Et2O layer was separated and dried (MgSO4), and the Et2O evaporated. The residue was recrystallized from C6H6 (x3) to yield the title compound, 24.5 g (21%), mp 149°-151°. Anal. (C11H7F3O3) C, H, F.

Workup

  1. temperatureat reflux
  2. temperaturethe mixture was cooled
  3. customThe Et2O layer was separated
  4. dry with materialdried (MgSO4)
  5. customthe Et2O evaporated
  6. customThe residue was recrystallized from C6H6 (x3)

Sources & evidence

ORD record
ord-2979481f93224973a4952050fa7c89f9
Source dataset
uspto-grants-1976_04
Patent number
US03953463

Reaction notes

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