Iodine → 1-Chloro-3-(2-chlorophenyl)propan-2-one

HRID 1671636Notes

Reaction equation

HRID 1671636 reaction equation
[Cl:1][CH2:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](Cl)=[C:7](Cl)[CH:6]=1.[Cl:14]C1C=CC=CC=1CCl.II.ClCC(Cl)=O>[Zn].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][CH2:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:14]

Participants

7

Reactant 4

HCID 807IodineHCID 6577Chloroacetyl chlorideHCID 119062-Chlorobenzyl chlorideHCID 161001771-Chloro-3-(3,4-dichlorophenyl)propan-2-one

Product 1

HCID 161002051-Chloro-3-(2-chlorophenyl)propan-2-oneYield 22%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

The procedure described above for the synthesis of 1-chloro-3-(3,4-dichlorophenyl)propan-2-one was followed, reacting 2-chlorobenzyl chloride (1.6 mL, 2.0 g, 12 mmol) with zinc dust (1.22 g, 18.6 mmol) in the presence of iodine (0.157 g, 0.620 mmol), then with chloroacetyl chloride (1.5 mL, 2.1 g, 19 mmol) in the presence of Pd(PPh3)4 (0.287 g, 0.248 mmol). Flash chromatography over silica gel (10% ethyl acetate in hexanes) gave product of sufficient purity to be used in the next step (0.556 g, 22% yield): 1H NMR (400 MHz, CDCl3) δ 4.03 (s, 2H) 4.19 (s, 2H) 7.19-7.29 (m, 3H) 7.38-7.42 (m, 1H).

Workup

  1. customFlash chromatography over silica gel (10% ethyl acetate in hexanes) gave product of sufficient purity

Sources & evidence

ORD record
ord-f1baccaeebdb4b9ea6615c1eb31a037f
Source dataset
uspto-grants-2011_08
Patent number
US07994333B2

Reaction notes

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