Sodium Chloride → 3-Ethoxybenzo[D]isoxazol-6-OL

HRID 1513304Notes

Reaction equation

HRID 1513304 reaction equation
B(Br)(Br)Br.O1C2C=CC=CC=2C=N1.[CH2:14]([O:16][C:17]1[C:21]2[CH:22]=[CH:23][C:24]([O:26]C)=[CH:25][C:20]=2[O:19][N:18]=1)[CH3:15].C([O-])(O)=O.[Na+].[Na+].[Cl-]>ClCCl.O.CCCCCC.C(OCC)(=O)C>[CH2:14]([O:16][C:17]1[C:21]2[CH:22]=[CH:23][C:24]([OH:26])=[CH:25][C:20]=2[O:19][N:18]=1)[CH3:15]

Participants

9

Reactant 5

HCID 5234Sodium ChlorideHCID 25134Boron tribromideHCID 710731,2-BenzisoxazoleHCID 516892Sodium BicarbonateHCID 210778053-Ethoxy-6-methoxybenzo[D]isoxazole

Product 1

HCID 1358487453-Ethoxybenzo[D]isoxazol-6-OL

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Boron tribromide (1.0M solution in dichloromethane; 1.39 ml, 1.39 mmol) was added to a stirred, −78° cooled solution of benzisoxazole from part (c) (179 mg, 928 μmol) in dichloromethane (4 ml) under an argon atmosphere. The reaction mixture was gradually warmed to room temperature over approx. 2 hours, and stirred overnight. Tlc (silica, 2:1 hexane/ethyl acetate) showed new polar material as well as unreacted starting material. The reaction was worked up by adding water (5 ml) and ice. The aqueous phase was neutralized by addition of saturated NaHCO3 solution, and saturated with NaCl. The aqueous phase was extracted into dichloromethane (3×60 ml), then the organic extracts combined and washed with brine (10 ml) and dried (NaSO4). The product was purified by chromatography on silica (18 g; eluent 2.5%, 5%, then 15% ethyl acetate/hexane). The first compound to elute was unreacted 3-ethoxy-6-methoxy-1,2-benzisoxazole, (46 mg), followed by 3-ethoxy-6-hydroxy-1,2-benzisoxazole 108 mg (65%).

Workup

  1. extractionThe aqueous phase was extracted into dichloromethane (3×60 ml)
  2. washwashed with brine (10 ml)
  3. dry with materialdried (NaSO4)
  4. customThe product was purified by chromatography on silica (18 g
  5. washThe first compound to elute

Sources & evidence

ORD record
ord-771e279540764057960214ef768ba6f5
Source dataset
uspto-grants-2012_07
Patent number
US08217171B2

Reaction notes

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