Triphenyl phosphite → 2,2,2-Trifluoro-1-[3-(trifluoromethyl)phenyl]ethan-1-ol

HRID 587188Notes

Reaction equation

HRID 587188 reaction equation
BrC(C1C=C(Cl)C=C(Cl)C=1)[C:3]([F:6])([F:5])[F:4].Cl[C:16]1[CH:17]=[C:18]([CH:23]([OH:28])[C:24]([F:27])([F:26])[F:25])[CH:19]=[C:20](Cl)[CH:21]=1.C1C(=O)N(Br)C(=O)C1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>C(Cl)Cl>[F:25][C:24]([F:27])([F:26])[CH:23]([C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:3]([F:6])([F:5])[F:4])[CH:17]=1)[OH:28]

Participants

6

Reactant 4

HCID 7540Triphenyl phosphiteHCID 67184N-bromobutanimideHCID 616446851-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanolHCID 866751181-(1-Bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzene

Product 1

HCID 2445592,2,2-Trifluoro-1-[3-(trifluoromethyl)phenyl]ethan-1-olYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

1-(1-Bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzene (AI1). To a stirred solution of 1-(3,5-dichlorophenyl)-2,2,2-trifluoroethanol (4.0 g, 16.3 mmol) in CH2Cl2 (50 mL), were added NBS (2.9 g, 16.3 mmol) and triphenyl phosphite (5.06 g, 16.3 mmol), and the resultant reaction mixture was heated at reflux for 18 h. After the reaction was deemed complete by TLC, the reaction mixture was cooled to 25° C. and was concentrated under reduced pressure. Purification by flash column chromatography (SiO2, 100-200 mesh; eluting with 100% pentane) afforded the title compound as a liquid (2.0 g, 40%): 1H NMR (400 MHz, CDCl3) δ 7.41 (s, 3H), 5.00 (m, 1H); EIMS m/z 306 ([M]+).

Workup

  1. customthe resultant reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 18 h
  4. concentrationwas concentrated under reduced pressure
  5. customPurification
  6. washby flash column chromatography (SiO2, 100-200 mesh; eluting with 100% pentane)

Sources & evidence

ORD record
ord-615497d5e4d14abe91fd9b0f707625a6
Source dataset
uspto-grants-2016_01
Patent number
US09226500B2

Reaction notes

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