Chloroform → 4-Bromo-2,6-diisopropylaniline

HRID 895947Notes

Reaction equation

HRID 895947 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].[Br:14]Br.C(Cl)(Cl)Cl.[OH-].[Na+]>CO>[Br:14][C:9]1[CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]([NH2:6])=[C:7]([CH:11]([CH3:13])[CH3:12])[CH:8]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 24408BromineHCID 32484Diisopropylaniline

Product 1

HCID 117801144-Bromo-2,6-diisopropylaniline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,6-diisopropylaniline (2.0 mL, 11 mmol) in methanol (80 mL) was treated dropwise with bromine (543 μL, 10.6 mmol). The solution was stirred at room temperature for 15 min. Chloroform and 0.1 N NaOH were added and the organic layer was dried (Na2SO4), filtered and concentrated to an orange liquid. Kugelrohr distillation (110° C. @ 0.06 Torr) afforded a colorless liquid (2.22 g 79%): 1H NMR (400 MHz) δ1.25 (d, J=6.4 Hz, 12H), 2.88 (m, 2H), 3.70 (brs, 2H), 7.11 (s, 2H); 13C NMR δ22.1, 27.9, 111.0, 125.6, 134.5, 139.3; Anal calcd for C12H19BrN: C, 56.26; H, 7.08; Br, 31.19; Found, C, 56.24; H, 7.07; Br, 30.98.

Workup

  1. dry with materialthe organic layer was dried (Na2SO4)
  2. filtrationfiltered
  3. concentrationconcentrated to an orange liquid
  4. distillationKugelrohr distillation (110° C. @ 0.06 Torr)
  5. customafforded a colorless liquid (2.22 g 79%)

Sources & evidence

ORD record
ord-cc681ff3cdaa4b2bb1342791086ea934
Source dataset
uspto-grants-2005_07
Patent number
US06916982B2

Reaction notes

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