Methyl 3,3,3-trifluoro-2-hydroxy-2-methylpropanoate → 2-[2-(3-Bromo-phenyl)-2-oxo-ethoxy]-3,3,3-trifluoro-2-methyl-propionic acid methyl ester

HRID 2196252Notes

Reaction equation

HRID 2196252 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]([OH:10])([CH3:9])[C:5]([F:8])([F:7])[F:6].[Br:12][C:13]1[CH:14]=[C:15]([C:19](=[O:23])[CH:20]=[N+]=[N-])[CH:16]=[CH:17][CH:18]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O.C(O)(C(F)(F)F)=O.C(O)(C(F)(F)F)=O.C(O)(C(F)(F)F)=O.[Rh].[Rh]>[CH3:1][O:2][C:3](=[O:11])[C:4]([O:10][CH2:20][C:19]([C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([Br:12])[CH:14]=1)=[O:23])([CH3:9])[C:5]([F:7])([F:6])[F:8]

Participants

5

Reactant 2

HCID 13384224Methyl 3,3,3-trifluoro-2-hydroxy-2-methylpropanoateHCID 543428411-(3-Bromophenyl)-2-diazonioethen-1-olate

Product 1

HCID 666655732-[2-(3-Bromo-phenyl)-2-oxo-ethoxy]-3,3,3-trifluoro-2-methyl-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 1098518731126-95-1CatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3,3,3-trifluoro-2-hydroxy-2-methyl-propionic acid methyl ester (22.94 g, 133 mmol) in CH2Cl2 (400 ml) was added rhodium(II) trifluoroacetate dimer (0.439 g, 0.667 mmol). After cooling to 0° C. a solution of 1-(3-bromo-phenyl)-2-diazo-ethanone (15.0 g, 66.7 mmol) dissolved in CH2Cl2 (100 ml) was added over a period of 2 h. The reaction mixture was concentrated and the title compound was obtained after flash-chromatography on silica gel (toluene) as a yellow oil: TLC (toluene/EtOAc 10:1): Rf=0.45; HPLC RtH5=1.352 min; 1H NMR (360 MHz, CDCl3): δ 8.15 (s, 1H), 7.94 (d, 1H), 7.76 (d, 1H), 7.40 (t, 1H), 4.87 (s, 2H), 3.89 (s, 3H), 1.72 (s, 3H); ESIMS: 386, 388 [(M+NH4)+].

Workup

  1. additionwas added over a period of 2 h
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-56a1b78c4e15430bb49e6d8d193d18f6
Source dataset
uspto-grants-2012_12
Patent number
US08338413B1

Reaction notes

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