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Reaction

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

HRID 1671636

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 Procedure Workup Sources & evidence Reaction notes

Participants

7

Reactant 4

HCID 6577Chloroacetyl chloride

HCID 119062-Chlorobenzyl chloride

HCID 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 23994

Zinc

Catalyst

HCID 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

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
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994333B2

Reaction notes

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On this pageParticipants Procedure Workup Sources & evidence Reaction notes