Hydrochloric Acid → 3-(Benzyloxy)-2-bromo-5-(5-methyloxazol-2-yl)phenol

HRID 1027247Notes

Reaction equation

HRID 1027247 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([C:26]2[O:27][C:28]([CH3:31])=[CH:29][N:30]=2)[CH:13]=[C:14]([O:17]COCC[Si](C)(C)C)[C:15]=1[Br:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1COCC1.O>[CH2:2]([O:9][C:10]1[C:15]([Br:16])=[C:14]([OH:17])[CH:13]=[C:12]([C:26]2[O:27][C:28]([CH3:31])=[CH:29][N:30]=2)[CH:11]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 867106522-(3-(Benzyloxy)-4-bromo-5-((2-(trimethylsilyl)ethoxy)methoxy)phenyl)-5-methyloxazole

Product 1

HCID 867106553-(Benzyloxy)-2-bromo-5-(5-methyloxazol-2-yl)phenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Concentrated hydrochloric acid (3 mL) was added to a solution of 2-(3-(benzyloxy)-4-bromo-5-((2-(trimethylsilyl)ethoxy)methoxy)phenyl)-5-methyloxazole (0.60 g, 1.22 mmol) in THF (8 mL) and stirred at room temperature for three hours. The solution was diluted with water and extracted with 1:1 ethyl acetate/diethyl ether (4×). The extracts were washed with saturated sodium bicarbonate, brine, dried over magnesium sulfate and concentrated to a solid. The solid was triturated with heptane (2×) and dried under vacuum to provide 3-(benzyloxy)-2-bromo-5-(5-methyloxazol-2-yl)phenol as an off white solid (412 mg). MS (M+1)=360.2. 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. extractionextracted with 1:1 ethyl acetate/diethyl ether (4×)
  2. washThe extracts were washed with saturated sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to a solid
  5. customThe solid was triturated with heptane (2×)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-25632215d20a426ab144a0423926bb04
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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