Ethyl Bromide → HCID 58554210, compound

HRID 1630997Notes

Reaction equation

HRID 1630997 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH3:30]>C(#N)C>[CH2:29]([O:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:19])([F:20])[F:21])[CH3:30]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 58554189HCID 58554189, compound

Product 1

HCID 58554210HCID 58554210, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 2-hydroxy-2′-(trifluoromethyl)biphenyl-4-carboxylate (5.03 g), anhydrous potassium carbonate (7.05 g, 51 mmol) and bromoethane (6.35 mL, 85 mmol) was prepared in anhydrous ACN (75 mL) and heated at 50° C. for 15 hours. The reaction mixture was cooled at RT, filtered and concentrated under reduced pressure. After purification by flash chromatography (silica, EtOAc/heptane), the title was obtained as a colorless oil (4.45 g, 79% over 2 steps). HPLC (Method A), Rt: 5.3 min (purity: 99.0%). UPLC/MS, M+(ESI): 325.0.

Workup

  1. temperatureThe reaction mixture was cooled at RT
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customAfter purification by flash chromatography (silica, EtOAc/heptane)
  5. customthe title was obtained as a colorless oil (4.45 g, 79% over 2 steps)

Sources & evidence

ORD record
ord-434fdc457fd24b6b939596219958af8f
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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