tert-Butyl 5-bromo-2-chlorobenzoate → HCID 67215392, compound

HRID 2421038Notes

Reaction equation

HRID 2421038 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:15])=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]>CO.C(N(CC)C(C)C)(C)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:15][C:5]1[CH:4]=[CH:3][C:2]([C:7]([O:9][CH3:10])=[O:8])=[CH:14][C:6]=1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

5

Reactant 1

HCID 22291846tert-Butyl 5-bromo-2-chlorobenzoate

Product 1

HCID 67215392HCID 67215392, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 81531DiisopropylethylamineSolvent

Procedure

tert-Butyl 5-bromo-2-chlorobenzoate (1.9 g) (WO2003095430) was dissolved in methanol (18 ml) with N,N-diisopropylethylamine (2 mL) and dichlorobis(triphenylphosphine)-palladium(II) (0.134 g). The mixture was carbonylated at 85° C. for 12 h. The cooled solution was evaporated and purified by flash chromatography, eluting with 5:95 ethyl acetate/isohexane, to yield the subtitle compound as a colourless oil (0.67 g).

Workup

  1. customThe cooled solution was evaporated
  2. custompurified by flash chromatography
  3. washeluting with 5:95 ethyl acetate/isohexane

Sources & evidence

ORD record
ord-1ae9bdc4a40347f4a4531ffe6dfe7170
Source dataset
uspto-grants-2011_06
Patent number
US07956070B2

Reaction notes

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