N-bromobutanimide → 1-(Bromomethyl)-4-chloro-2-iodobenzene

HRID 1348883

Reaction equation

HRID 1348883 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([I:9])[CH:3]=1.[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:10][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[I:9]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 141766Benzene, 4-chloro-2-iodo-1-methyl-

Product 1

HCID 129309611-(Bromomethyl)-4-chloro-2-iodobenzeneYield 64.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-chloro-2-iodo-1-methylbenzene (3.95 g, 15.6 mmol), N-bromosuccinimide (3.10 g, 17.6 mmol), and benzoyl peroxide (0.1 g) in carbon tetrachloride (100 mL) was heated to reflux for 48 hours, filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 4:100 ethyl acetate/hexanes to provide 3.34 g (64%) of the desired product. MS (DCI/NH3) m/z 330, 332 (M+H)30; 1H NMR (CDCl3) δ 7.85 (d, 1H), 7.40-7.32 (m, 2H), 4.59 (s, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 hours
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 4:100 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0c73544aaf074639b176ee31bd481435
Source dataset
uspto-grants-2007_05
Patent number
US07211595B2

Linked notes

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