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

HRID 1503655Notes

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>ClCCl>[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

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 dichloromethane (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

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

Sources & evidence

ORD record: ord-6d1ced11fd1d4763a70055557da1947d
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212164B2

Reaction notes

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