Hydrochloric Acid → 7-Bromo-1-(4-nitrophenyl)-isochromane

HRID 1018451Notes

Reaction equation

HRID 1018451 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[N+:11]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)([O-:13])=[O:12].Cl>C1C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([CH2:8][CH2:9][O:10][CH:18]2[C:17]2[CH:20]=[CH:21][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5414-NitrobenzaldehydeHCID 728512-(4-Bromophenyl)ethanol

Product 1

HCID 184014877-Bromo-1-(4-nitrophenyl)-isochromane

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 241BenzeneSolvent

Procedure

20.1 g (100 mM) of 2-(4-bromophenyl)-ethanol and 15.1 g (100 mM) of 4-nitrobenzaldehyde were dissolved in 300 ml of anhydrous benzene, then 13.6 g (100 mM) of anhydrous zinc chloride were added and dry hydrochloric acid gas was led into the stirred mixture for 4 hours. Then the process described under Examples 1-7, Step a) was applied. The crude product was recrystallized from ethyl acetate.

Workup

  1. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8ac75809898240ffa4bcf3d7a00f6bbe
Source dataset
uspto-grants-2002_11
Patent number
US06482819B1

Reaction notes

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