Trifluoroacetic acid → HCID 58290283, compound
Reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([C:5]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:6]=1[F:12])=O.[CH:15]([N:18](CC)[CH:19]([CH3:21])C)(C)[CH3:16].[BH3-]C#N.[Na+].FC(F)(F)C(O)=[O:31].C([O-])(O)=O.[Na+]>ClCCl.Cl[Ti](Cl)(Cl)Cl.CO>[F:1][C:2]([F:14])([F:13])[CH:3]([N:18]1[CH2:19][CH2:21][O:31][CH2:16][CH2:15]1)[C:5]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:6]=1[F:12]Participants
9
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of commercially available 2,2,2-trifluoro-1-(2-fluoro-5-iodophenyl)ethanone (2 g, 6.29 mmol) in 20 mL dichloromethane at rt was added N,N-diisopropylethylamine (3.3 mL, 18.95 mmol, 3 eq.) followed by 1M solution of TiCl4 in dichloromethane (6.3 mL, 6.3 mmol, 1 eq.). The mixture was stirred at rt for 3 days, added 10 mL of methanol followed by NaCNBH3 (3.2 g) and trifluoroacetic acid (4.7 mL). The mixture was stirred overnight at rt, poured into aq. NaHCO3 and extracted 3× with dichloromethane. The combined organic layer was washed with brine, dried over MgSO4, filtered, concentrated and purified by chromatography eluting with 0% to 20% ethyl acetate in hexane to provide 1.16 g of MCH14-1.
Workup
- stirringThe mixture was stirred overnight at rt
- extractionextracted 3× with dichloromethane
- washThe combined organic layer was washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- custompurified by chromatography
- washeluting with 0% to 20% ethyl acetate in hexane
- customto provide 1.16 g of MCH14-1
Sources & evidence
- ORD record
- ord-2e3c82c5b9bb4337974756981568a517
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987242B2
Reaction notes
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