Phosphorus tribromide → HCID 90402480, compound

HRID 576701Notes

Reaction equation

HRID 576701 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:12](O)[CH3:13].P(Br)(Br)[Br:16].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:16][CH:12]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([F:11])([F:10])[F:9])[C:2]=1[Cl:1])[CH3:13]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 90013412HCID 90013412, compound

Product 1

HCID 90402480HCID 90402480, compoundYield 194.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled solution of (±)-1-(2-chloro-3-(trifluoromethyl)phenyl)ethanol (1.1 g, 4.9 mmol) in DCM (16 mL) was added phosphorus tribromide (0.23 mL, 2.5 mmol) dropwise. The reaction was allowed to warm to rt and stirred for 3 h. Saturated aqueous NaHCO3 was added, and the mixture was extracted with DCM (×3). The combined organic extracts were dried (Na2SO4), filtered, and concentrated to give the desired product as a yellow oil (1.4 g, 97%). 1H NMR (400 MHz, CDCl3) δ 7.93-7.81 (m, 1H), 7.69-7.64 (m, 1H), 7.42 (t, J=7.9 Hz, 1H), 5.73 (q, J=7.0 Hz, 1H), 2.05 (d, J=7.0 Hz, 3H).

Workup

  1. extractionthe mixture was extracted with DCM (×3)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-be1108faccdd469bbb62a76ac6fc2869
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

Loading…