Boron tribromide → 5-[4-(5-Chloro-2-hydroxy-phenyl)-oxazol-2-yl]-pentanoic acid

HRID 1616629Notes

Reaction equation

HRID 1616629 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][CH:10]=[C:11]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[O:20]C)[N:12]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:19][C:17]1[CH:16]=[CH:15][C:14]([OH:20])=[C:13]([C:11]2[N:12]=[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:22])=[O:2])[O:9][CH:10]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 591677715-[4-(5-Chloro-2-methoxy-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester

Product 1

HCID 684898155-[4-(5-Chloro-2-hydroxy-phenyl)-oxazol-2-yl]-pentanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 5-[4-(5-Chloro-2-methoxy-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester (0.32 g, 1.0 mmol) in CH2Cl2 (2 mL) under nitrogen at RT. Add boron tribromide (1M in CH2Cl2, 3 mL) and stir at RT until the reaction is complete. Quench the mixture into water and extract with EtOAc. Dry the combined extracts over Na2SO4 and concentrate. Chromatograph the resulting residue over silica gel (MeOH/CH2Cl2) to allow for isolation of 5-[4-(5-chloro-2-hydroxy-phenyl)-oxazol-2-yl]-pentanoic acid (0.27 g, 91%). MS (ES): (M+1)+ 296.1, 298.1 m/z.

Workup

  1. customQuench the mixture into water
  2. extractionextract with EtOAc
  3. dry with materialDry the combined extracts over Na2SO4
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-1822cb8b51b241b99032bb28a00e5440
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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