2-Isopropylaniline → 4-Bromo-2-(propan-2-yl)aniline

HRID 1170953Notes

Reaction equation

HRID 1170953 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([CH3:3])[CH3:2].[Br:11]Br>ClCCl>[Br:11][C:9]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:10]=1

Participants

4

Reactant 2

HCID 125612-IsopropylanilineHCID 24408Bromine

Product 1

HCID 222719374-Bromo-2-(propan-2-yl)anilineYield 135.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled solution of 2-iso-propyl aniline (714 mg, 5.28 mmol) in dichloromethane (20 mL) at −50° C. in a dry ice/acetone bath was added a solution of bromine (269 μl, 5.28 mmol) in dichloromethane (5 mL) over 20 min. After completion of the addition, the reaction mixture was stirred for an additional hour. Purification by column chromatography (silica gel, hexane/ethyl acetate) gave 4-bromo-2-iso-propyl-phenylamine as a brown oil (1.53 g, 57%); 1H NMR (300 MHz, DMSO-d6): δ 7.01 (m, 2H), 6.55 (d, 1H, J=13 Hz), 5.05 (bs, 2H), 2.92 (m, 1H), 1.11 (d, 6H, J=7 Hz); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=Hexane/ethyl acetate [10:1]; Rf=0.11

Workup

  1. additionAfter completion of the addition
  2. customPurification by column chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-dc8dfd28d0594e25a61b6d96b95fc121
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

Loading…