1,4-Dibromobenzene → 4-bromo-N-hexylaniline

HRID 984681Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[CH2:9]([NH2:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:15][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:3][CH:4]=1

Participants

Reactant 2

HCID 78041,4-Dibromobenzene

HCID 8102Hexylamine

Product 1

HCID 219406454-bromo-N-hexylanilineYield 83%

Procedure

Using the general procedure, 1,4-dibromobenzene (236 mg, 1.0 mmol) was coupled with n-hexylamine (158 μL, 1.2 mmol) at 90° C. for 20 h. Purification of the crude product by column chromatography on silica gel using hexane/ethyl acetate (20:1) as eluent afforded the desired product as a colorless oil (212 mg, 83% yield). Rf=0.6 (hexane/ethyl acetate=10:1).

Workup

customPurification of the crude product by column chromatography on silica gel

Sources & evidence

ORD record: ord-7168601c64b74d419a26bddb8c8de40d
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867298B2

Reaction notes

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