Sulfuric Acid → HCID 2778117, compound

HRID 1580171Notes

Reaction equation

[Cl:1][C:2]1[CH:8]=[CH:7][C:5](N)=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].N([O-])=O.[Na+].S(=O)(=O)(O)O.[C:22]([OH:26])(=[O:25])[CH:23]=[CH2:24]>>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([CH:24]=[CH:23][C:22]([OH:26])=[O:25])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10]

Participants

Reactant 4

HCID 1118Sulfuric Acid

HCID 6581Acrylic Acid

HCID 675744-Chloro-3-(trifluoromethyl)aniline

HCID 23668193Sodium Nitrite

Product 1

HCID 2778117HCID 2778117, compound

Procedure

4-Chloro-3-trifluoromethyl aniline was converted to the diazonium salt with sodium nitrite and sulfuric acid and this was reacted with acrylic acid (Meerwein reaction) to give 4-chloro-3-trifluoromethyl cinnamic acid. This acid was hydrogenated, reduced with lithium aluminum hydride to the alcohol and reacted with phosphorus tribromide to give 3(4-chloro-3-trifluoromethylphenyl)propyl bromide.

Sources & evidence

ORD record: ord-c54784bfed7548f69b5167a0df1674a7
Source dataset: uspto-grants-1976_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03932432

Reaction notes

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