Potassium Hydroxide → Tert-butyl (3,4-dichloro-5-hydroxyphenyl)carbamate

HRID 38553Notes

Reaction equation

HRID 38553 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[C:12](Cl)[C:11]([Cl:15])=[C:10]([Cl:16])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-:18].[K+]>>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[C:12]([OH:18])[C:11]([Cl:15])=[C:10]([Cl:16])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 18929852N-(tert-Butoxycarbonyl)-3,4,5-trichloroaniline

Product 1

HCID 58116863Tert-butyl (3,4-dichloro-5-hydroxyphenyl)carbamate

Conditions

Temperature
90 °C

Procedure

In analogy to Example 63A, tert-butyl(3,4,5-trichlorophenyl)carbamate from Example 66A (3.98 g, 13.4 mmol) was reacted with potassium hydroxide (1.77 g, 26.8 mmol). The reaction mixture was heated to 80° C. overnight and subsequently to 90° C. for 3 h. The product was isolated by preparative HPLC to yield 760 mg (20%).

Workup

  1. customThe product was isolated by preparative HPLC
  2. customto yield 760 mg (20%)

Sources & evidence

ORD record
ord-2834e6463a5c4394b92d7a553004b9d3
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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