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

HRID 1443741Notes

Reaction equation

HRID 1443741 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 CH2C2, 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-d331a8300b394bda827f755f9fe8b7c4
Source dataset
uspto-grants-2010_02
Patent number
US07662771B2

Reaction notes

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