Ammonia → 3,5-Dichloroaniline

HRID 1390245Notes

Reaction equation

[NH3:1].[NH2-].[Na+].Br[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12]>>[Cl:12][C:6]1[CH:5]=[C:10]([CH:9]=[C:8]([Cl:11])[CH:7]=1)[NH2:1]

Participants

Reactant 3

HCID 222Ammonia

HCID 24533Sodium amide

HCID 709471-Bromo-2,4-dichlorobenzene

Product 1

HCID 122813,5-DichloroanilineYield 75.5%

Procedure

In the second step of Example 1, 500 ml of liquid ammonia, 10 g (0.25 mole) of sodium amide and 11.3 g (0.05 mole) of 1-bromo-2,4-dichlorobenzene were charged and the reaction was carried out for 1 hour to obtain 6.1 g of 3,5-dichloroaniline. (yield: 75.5%).

Sources & evidence

ORD record: ord-7b2306d28bda4da1adb56ee7163d7a02
Source dataset: uspto-grants-1979_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04138436

Reaction notes

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