Iodoethane → 2-(3-(Benzyloxy)-4-bromo-5-ethoxyphenyl)-5-methyloxazole

HRID 1027248Notes

Reaction equation

HRID 1027248 reaction equation
I[CH2:2][CH3:3].[CH2:4]([O:11][C:12]1[C:13]([Br:25])=[C:14]([OH:24])[CH:15]=[C:16]([C:18]2[O:19][C:20]([CH3:23])=[CH:21][N:22]=2)[CH:17]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.C(OCC)C>[CH2:4]([O:11][C:12]1[CH:17]=[C:16]([C:18]2[O:19][C:20]([CH3:23])=[CH:21][N:22]=2)[CH:15]=[C:14]([O:24][CH2:2][CH3:3])[C:13]=1[Br:25])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 867106553-(Benzyloxy)-2-bromo-5-(5-methyloxazol-2-yl)phenol

Product 1

HCID 867106562-(3-(Benzyloxy)-4-bromo-5-ethoxyphenyl)-5-methyloxazoleYield 95.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584169Diethylether ethylacetateSolvent

Procedure

Iodoethane (111 uL, 1.37 mmol) was added to a mixture of 3-(benzyloxy)-2-bromo-5-(5-methyloxazol-2-yl)phenol (412 mg, 1.14 mmol) and potassium carbonate (632 mg, 4.58 mmol) in DMF (2.8 mL). After stirring for two hours, the solution was diluted with 1:1 ethyl acetate/diethyl ether, washed with water (5×), brine, dried over magnesium sulfate and concentrated to provide 2-(3-(benzyloxy)-4-bromo-5-ethoxyphenyl)-5-methyloxazole as a white crystalline solid (421 mg). MS (M+1)=388.2. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.52 (d, J=7.07 Hz, 2H), 7.36-7.43 (m, 2H), 7.28-7.35 (m, 2H), 7.23 (d, J=1.52 Hz, 1H), 6.86 (d, J=1.52 Hz, 1H), 5.24 (s, 2H), 4.21 (q, J=6.74 Hz, 2H), 2.41 (d, J=1.01 Hz, 3H), 1.50 (t, J=6.82 Hz, 3H).

Workup

  1. washwashed with water (5×), brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f45a5fdfe8aa4c01b71ae63fce4474e8
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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