Bromine → HCID 21102188, compound

HRID 2355956Notes

Reaction equation

HRID 2355956 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[NH2:11])([CH3:3])[CH3:2].[Br:12]Br>C(O)(=O)C.C(Cl)Cl>[Br:12][C:8]1[CH:7]=[C:6]([CH3:10])[C:5]([NH2:11])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:9]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 789206-Isopropyl-o-toluidine

Product 1

HCID 21102188HCID 21102188, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

2-Isopropyl-6-methyl-phenylamine (5 g, 33.5 mmol) was dissolved in acetic acid (20 mL). To this solution was added a solution of bromine (1.8 mL, 35.14 mmol) in acetic acid (5 mL) dropwise over 10 min. After stirring for 1 h at room temperature, the reaction mixture was diluted with methylene chloride, washed with water (2×), saturated sodium thiosulfate (2×), saturated sodium bicarbonate (2×), and brine. The organic phase was dried over sodium sulfate, filtered, and concentrated. Purification by flash chromatography on silica gel afforded 7.6 g (quantitative) of the desired product. LC/MS: tR=1.37 min, 230.07 (MH)+.

Workup

  1. washwashed with water (2×), saturated sodium thiosulfate (2×), saturated sodium bicarbonate (2×), and brine
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-53054fc6f2674f7a966d77ff97c47160
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

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