1-Chloro-4-(chloromethyl)benzene → HCID 57438717, compound

HRID 2354504Notes

Reaction equation

HRID 2354504 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:18][C:17]2[CH:20]=[CH:21][C:14]([Cl:13])=[CH:15][CH:16]=2)[C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 10796Cesium carbonateHCID 57438716HCID 57438716, compound

Product 1

HCID 57438717HCID 57438717, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a vigorously stirred solution of (3-bromo-5-chlorophenyl)acetone (4.0 g, 17 mmol) and 4-chlorobenzyl chloride (2.2 g, 14 mmol) in 60 mL of acetonitrile at 0° C. was added cesium carbonate (11 g, 35 mmol), and the reaction was allowed to warm to room temperate overnight. The reaction mixture was partitioned between ethyl acetate (200 mL) and saturated aqueous ammonium chloride (200 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to afford the title compound. 1H NMR (500 MHz, CD3OD): δ 7.21 (s, 1H), 7.19 (d, 2H), 7.04 (d, 2H), 6.97 (d, 1H), 6.87 (d, 1H), 4.16 (dd, 1H), 3.25 (dd, 1H), 2.86 (dd, 1H), 2.03 (s, 3H).

Workup

  1. temperatureto warm to room temperate overnight
  2. customThe reaction mixture was partitioned between ethyl acetate (200 mL) and saturated aqueous ammonium chloride (200 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e8c4a75a773a490695f7fb885dcc9f22
Source dataset
uspto-grants-2010_07
Patent number
US07754188B2

Reaction notes

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