Dichloromethane → HCID 10863893, compound

HRID 990503Notes

Reaction equation

HRID 990503 reaction equation
ClCCl.[Br:4][C:5]1[CH:6]=[C:7]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:25])([F:24])[CH:21]([F:23])[F:22])[CH:14]=2)[CH:8]=[CH:9][CH:10]=1.[F:26][C:27]([F:32])([F:31])[CH:28]1[O:30][CH2:29]1.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3]>C(OCC)C>[Br:4][C:5]1[CH:6]=[C:7]([N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:24])([F:25])[CH:21]([F:23])[F:22])[CH:14]=2)[CH2:29][CH:28]([OH:30])[C:27]([F:32])([F:31])[F:26])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 5207692-(Trifluoromethyl)oxiraneHCID 2733225Ytterbium triflateHCID 11036219HCID 11036219, compound

Product 1

HCID 10863893HCID 10863893, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a dichloromethane (9 mL) solution of the EX-220A amine (3.27 g, 8.65 mmol) was added 1,1,1-trifluoro-2,3-epoxypropane (0.968 mL, 11.3 mmol) and Yb(OTf)3 (0.536 g, 0.86 mmol). The cloudy mixture was stirred at room temperature for 24 hours, then diluted with diethyl ether. The organic layer was washed with water and brine, dried (MgSO4) and evaporated to yield 4.20 g (99%) of the desired 3-[(3-bromophenyl)-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amino]-1,1,1-trifluoro 2-propanol product as a pale brown oil which can be used without further purification. The formation of the desired product was confirmed by the presence of the alcohol peak (δ1.5, d) in the 1H NMR spectrum (C6D6). An analytical sample was purified by silica gel chromatography eluting with 20% ethyl acetate in hexane to give the desired pure product as a yellow oil. FABMS m/z=491 [M+H+. 1H NMR (CDCl3) δ3.55-3.63 (m. 1H), 3.88 (dd, 1H), 4.36 (m, 1H), 4.69 (s, 2H), 5.914 (tt, 1H), 6.66 (dd, 1H), 6.92 (m, 2H), 7.06 (s, 1H), 7.09 (m, 3H), 7.36 (t, 1H).

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-3303b05b59f74c15a7b239d4686e210e
Source dataset
uspto-grants-2002_10
Patent number
US06458852B1

Reaction notes

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