Boron tribromide → 5-[5-(2-Hydroxy-phenyl)-isoxazol-3-yl]-pentanoic acid ethyl ester

HRID 1616596Notes

Reaction equation

HRID 1616596 reaction equation
B(Br)(Br)Br.[CH2:5]([O:7][C:8](=[O:26])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24]C)[O:15][N:14]=1)[CH3:6]>C(Cl)Cl>[CH2:5]([O:7][C:8](=[O:26])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[OH:24])[O:15][N:14]=1)[CH3:6]

Participants

4

Reactant 2

HCID 25134Boron tribromide3×HCID 591677545-[5-(2-Methoxy-phenyl)-isoxazol-3-yl]-pentanoic acid ethyl ester

Product 1

HCID 1362065315-[5-(2-Hydroxy-phenyl)-isoxazol-3-yl]-pentanoic acid ethyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add boron tribromide (43 mL, 43 mmol, 1.0 M solution in CH2Cl2) dropwise over 30 minutes to a stirred 0° C. solution of 5-[5-(2-methoxy-phenyl)-isoxazol-3-yl]-pentanoic acid ethyl ester (5.20 g, 17.1 mmol) in CH2Cl2 (45 mL). Allow to warm to room temperature overnight. Add boron tribromide (17 mL, 17 mmol, 1.0 M solution in CH2Cl2) and stir at room temperature under N2. After 4 hours, add boron tribromide (17 mL, 17 mmol, 1.0 M solution in CH2Cl2) and stir at room temperature under N2. After 2 hours, quench via dropwise addition of ethanol (50 mL, absolute). Concentrate, dissolve residue in CHCl3, wash with saturated NaHCO3 solution (×2), dry over MgSO4 and concentrate to get 4.7 g of a tan solid. Adsorb on SiO2 and purify the residue by flash chromatography on silica gel eluting with 3-20% EtOAc/hexanes to afford the title compound (3.96 g, 80%). MS (IS) 290 (M+1)+.

Workup

  1. waitAfter 2 hours
  2. customquench via dropwise addition of ethanol (50 mL, absolute)
  3. concentrationConcentrate
  4. dissolutiondissolve residue in CHCl3
  5. washwash with saturated NaHCO3 solution (×2)
  6. dry with materialdry over MgSO4
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-f868063f28db4c3c88cab82de0127a1b
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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