2-Bromopropane → 2-Isopropoxy-4-trifluoromethyl-benzoic acid isopropyl ester

HRID 1042471Notes

Reaction equation

[OH:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:15](=O)([O-])[O-].[K+].[K+].Br[CH:22]([CH3:24])[CH3:23].CCO[C:28]([CH3:30])=O>CN(C=O)C>[CH:22]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([C:11]([F:12])([F:13])[F:14])=[CH:10][C:2]=1[O:1][CH:28]([CH3:30])[CH3:15])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-hydroxy-4-trifluoromethyl-benzoic acid (500 mg, 2.42 mmol) in DMF (5 mL) was added potassium carbonate (837 mg, 6.06 mmol) and 2-bromopropane (906 mg, 5.33 mmol). The resulting mixture was stirred for 48 hours at 110° C. The reaction mixture was diluted with EtOAc, which was washed with 1N HCl, water, and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by chromatography (Hex/EtOAc=5/1) to give the title compound (200 mg, 28%).

Workup

washwas washed with 1N HCl, water, and brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude residue was purified by chromatography (Hex/EtOAc=5/1)

Sources & evidence

ORD record: ord-4c9d40553a354213a874c696b3584442
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557872B2

Reaction notes

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