Iodoethane → 1-Bromo-2-ethoxy-4-phenoxybenzene

HRID 449100Notes

Reaction equation

HRID 449100 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[OH:15].C(=O)([O-])[O-].[K+].[K+].I[CH2:23][CH3:24]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[O:15][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 189257712-Bromo-5-phenoxyphenol

Product 1

HCID 215249131-Bromo-2-ethoxy-4-phenoxybenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 2-bromo-5-phenoxyphenol (120 mg, 0.45 mmol) in acetone (7 mL) was added potassium carbonate (0.375 g, 2.72 mol) followed by iodoethane (0.0724 mL, 0.905 mol) at rt. The mixture was stirred at rt overnight. Reaction mixture was concentrated down in vacuo and washed with brine extracting with EtOAc. The organics were combined, dried over Na2SO4 and concentrated to afford the title compound which was used for next step without further purification. 1H NMR (400 MHz, CDCl3): δ=1.37 (t, J=6.95 Hz, 3H), 3.95 (q, J=7.07 Hz, 2H), 6.37 (dd, J=8.59, 2.78 Hz, 1H), 6.52 (d, J=2.53 Hz, 1H), 6.90-6.97 (m, 2H), 7.00-7.08 (m, 1H), 7.22-7.30 (m, 2H), 7.36 (d, J=8.59 Hz, 1H).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated down in vacuo
  3. washwashed with brine extracting with EtOAc
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fcc0eaa848ef4cd990cc1d13949f5e9f
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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