Potassium Carbonate → 5-Bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid 3-tert-butoxycarbonyl-propyl ester

HRID 1485992Notes

Reaction equation

HRID 1485992 reaction equation
[Br:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:13]([O:17][C:18](=[O:23])[CH2:19][CH2:20][CH2:21]Br)([CH3:16])([CH3:15])[CH3:14].[C:24]([O-:27])([O-])=[O:25].[K+].[K+]>CN(C=O)C>[C:13]([O:17][C:18]([CH2:19][CH2:20][CH2:21][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[C:3]([Cl:12])=[CH:4][C:5]=1[O:11][CH2:2][CH2:3][CH2:4][C:24]([O:27][C:6]([CH3:10])([CH3:7])[CH3:5])=[O:25])=[O:23])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2757253tert-Butyl 4-bromobutanoateHCID 110213535-Bromo-4-chloro-2-hydroxybenzoic acid

Product 1

HCID 686035915-Bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid 3-tert-butoxycarbonyl-propyl esterYield 153.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-4-chloro-2-hydroxy-benzoic acid (5 g, 19.9 mmol), 4-bromo-butyric acid tert-butyl ester (13.2 g, 59.7 mmol) and K2CO3 (11.1 g, 79.6 mmol) in DMF (100 mL) was heated at 80° C. for 2 days. The solid was filtered off. The solution was concentrated and purified via silica gel flash chromatography (eluting with 20% ethyl acetate in hexane) to give 5-bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid 3-tert-butoxycarbonyl-propyl ester (8.2 g). MS [M-iso-butene+H]+: 480.9; tR=3.32 min. (method 1)

Workup

  1. filtrationThe solid was filtered off
  2. concentrationThe solution was concentrated
  3. custompurified via silica gel flash chromatography (eluting with 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-28de3bc8eab74162a2ee87bb4ab0309f
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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