1,2-Dibromoethane → 1-(2-Bromoethoxy)-4-(trifluoromethoxy)benzene

HRID 513175Notes

Reaction equation

HRID 513175 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:19][CH2:20][CH2:21]Br>CC#N>[Br:19][CH2:20][CH2:21][O:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 70015p-(Trifluoromethoxy)phenol

Product 1

HCID 136722741-(2-Bromoethoxy)-4-(trifluoromethoxy)benzeneYield 52.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(trifluoromethoxy)phenol (1 g, 5.61 mmole) in CH3CN (20 mL) was added Cs2CO3 (3.66 g, 11.23 mmole) then 1,2-dibromoethane (2.42 mL, 28.1 mmole). The mixture was heated to reflux. After 3 days the mixture was cooled to RT, filtered through a pad of Celite washing with CH2Cl2, and concentrated. Flash column (Biotage-SNAP-50 g SiO2, 0-10% EtOAc/hexanes) gave the title compound (833 mg, 52%) as a clear liquid. 1H NMR (400 MHz, CDCl3): δ 7.15 (d, J=8.7 Hz, 2 H); 6.95-6.88 (m, 2 H); 4.29 (m, 2 H); 3.64 (t, J=6.29 Hz, 2H).

Workup

  1. temperatureThe mixture was heated to reflux
  2. filtrationfiltered through a pad of Celite
  3. washwashing with CH2Cl2
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-14c2497243e24e2ba0997c4838785ae6
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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