1-Chloro-4-iodobenzene → 4-Acetyl-4'-chloro-2-nitrobiphenyl

HRID 2071787Notes

Reaction equation

HRID 2071787 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH3:9][C:10]([C:12]1[CH:17]=[CH:16][C:15](Br)=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=1)=[O:11]>CO>[C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=1)(=[O:11])[CH3:9]

Participants

4

Reactant 2

HCID 125101-Chloro-4-iodobenzeneHCID 877371-(4-Bromo-3-nitrophenyl)ethan-1-one

Product 1

HCID 213205634-Acetyl-4'-chloro-2-nitrobiphenyl

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Chloroiodobenzene and 4-bromo-3-nitroacetophenone were reacted under Ullmann conditions to give the novel intermediate 4-acetyl-4'-chloro-2-nitrobiphenyl, m.p. 103°-105° C. (from methanol). This compound was reduced with stannous chloride and concentrated hydrochloric acid to give 4-acetyl-2-amino-4'-chlorobiphenyl, m.p. 139°-140° C. (from methanol).This compound was converted to the novel intermediate 4-acetyl-4'-chloro-2-hydroxybiphenyl and thence to the novel intermediate 4-acetyl-4'-chloro-2-methoxybiphenyl, b.p. 167°-170° C./0.4 mm., by diazotization and methylation methods analogous to those described in Example 1.

Sources & evidence

ORD record
ord-36c8d562051a4322807182b29d42812f
Source dataset
uspto-grants-1977_09
Patent number
US04048332

Reaction notes

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