Ethyl Bromide → HCID 66678423, compound

HRID 2410538Notes

Reaction equation

HRID 2410538 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=1[OH:19])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[CH3:27]>C(#N)C>[CH2:26]([O:19][C:10]1[CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=[CH:14][C:9]=1[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:1][CH3:2])[CH3:27]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 66678410HCID 66678410, compound

Product 1

HCID 66678423HCID 66678423, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of methyl 2′-ethyl-2-hydroxybiphenyl-4-carboxylate (3.13 g, 12.2 mmol) in anhydrous ACN (45 mL) was added anhydrous potassium carbonate (5.05 g, 36.6 mmol) followed by ethyl bromide (4.5 mL, 61 mmol). The reaction mixture was heated at 50° C. for 15 hours, and then cooled to RT and filtered. The filtrate was concentrated under vacuum. The oil was taken up with MTBE, treated with activated charcoal, filtered through a Celite pad and concentrated. After purification by flash chromatography (silica, heptane/EtOAc), the title compound was obtained as a colorless oil (2.73 g, 79%). HPLC (Method A) Rt 5.4 min (Purity: 99.7%).

Workup

  1. temperaturecooled to RT
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under vacuum
  4. additiontreated with activated charcoal
  5. filtrationfiltered through a Celite pad
  6. concentrationconcentrated
  7. customAfter purification by flash chromatography (silica, heptane/EtOAc)

Sources & evidence

ORD record
ord-22ab3ce1340749b4a09c59d278a7ff82
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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