Triphenyl phosphite → 1-(1-Bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzene

HRID 1502796Notes

Reaction equation

HRID 1502796 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9](O)[C:10]([F:13])([F:12])[F:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Br:15]N1C(=O)CCC1=O.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>C(Cl)Cl>[Br:15][CH:9]([C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=1)[C:10]([F:13])([F:12])[F:11]

Participants

5

Reactant 3

HCID 7540Triphenyl phosphiteHCID 67184N-bromobutanimideHCID 616446851-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanol

Product 1

HCID 866751181-(1-Bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzeneYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

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 N-bromosuccinimide (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-4168c8bc98cf40d9a7d1baeb7bcbff1a
Source dataset
uspto-grants-2015_12
Patent number
US09211280B2

Reaction notes

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