3-Chloro-2-iodophenol → Tert-butyl(3-chloro-2-iodophenoxy)acetate

HRID 2390179Notes

Reaction equation

HRID 2390179 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7]OC1C=CC(Cl)=CC=1Br)([CH3:4])([CH3:3])[CH3:2].[Cl:18][C:19]1[C:20]([I:26])=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=1>>[C:1]([O:5][C:6](=[O:17])[CH2:7][O:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([Cl:18])[C:20]=1[I:26])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 121757023-Chloro-2-iodophenolHCID 49766393tert-Butyl (2-bromo-4-chlorophenoxy)acetate

Product 1

HCID 16741488Tert-butyl(3-chloro-2-iodophenoxy)acetateYield 86%

Procedure

Following the general method as outlined in Intermediate 1, starting from 3-chloro-2-iodophenol (prepared as described in J. Org. Chem., 2005, 70, 6548-6551), the title compound was obtained as a white solid in 86% yield after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-3d0ecf57304b45aa95cd44b81b637080
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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