Boron tribromide → HCID 135988217, compound

HRID 1616637Notes

Reaction equation

HRID 1616637 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][C:7]1[O:11][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18]C)=[N:9][C:8]=1[CH3:20].B(Br)(Br)Br>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][C:7]1[O:11][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])=[N:9][C:8]=1[CH3:20]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59167805HCID 59167805, compound

Product 1

HCID 135988217HCID 135988217, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 4-[2-(2-methoxy-phenyl)-4-methyl-oxazol-5-yl]-butyric acid methyl ester (2.1 g, 7.3 mmol) in CH2Cl2 (20 mL) under nitrogen at room temperature. Add boron tribromide (1M in CH2Cl2, 21.8 mL) and stir at room temperature until the reaction is complete. Quench the mixture with methanol, add 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 4-[2-(2-hydroxy-phenyl)-4-methyl-oxazol-5-yl]-butyric acid methyl ester (1.55 g, 77%). MS (ES): (M+1)+ 276.1, 277.2 m/z.

Workup

  1. customQuench the mixture with methanol
  2. additionadd water
  3. extractionextract with CH2Cl2
  4. dry with materialDry the combined extracts over Na2SO4
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-9df298da29a74a4fa611fe97bc94857e
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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