Boron tribromide → 5-[4-(2-Hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester

HRID 1616632Notes

Reaction equation

HRID 1616632 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][C:10]([CH3:21])=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19]C)[N:12]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][C:10]([CH3:21])=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[N:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 591677855-[4-(2-Methoxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester

Product 1

HCID 684911055-[4-(2-Hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 5-[4-(2-methoxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester (3.5 g, 11.5 mmol) in CH2Cl2 (50 mL) under nitrogen at RT. Add boron tribromide (1M in CH2Cl2, 29 mL) and stir at RT until the reaction is complete. Quench the mixture into ice/water and extract with CH2Cl2. Dry the combined extracts over Na2SO4 and concentrate. Chromatograph the resulting residue over silica gel (MeOH/CH2Cl2) to allow for isolation of 5-[4-(2-hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester (2.61 g, 78%). MS (ES): (M+1)+ 290.2 m/z.

Workup

  1. customQuench the mixture into ice/water
  2. extractionextract with CH2Cl2
  3. dry with materialDry the combined extracts over Na2SO4
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-c2320b2236ad40c68ca630a5de2d187b
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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