Boron tribromide → HCID 136400604, compound

HRID 1039249Notes

Reaction equation

HRID 1039249 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[N:9]=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19]C)[S:11][CH:12]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[N:9]=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[S:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59167798HCID 59167798, compound

Product 1

HCID 136400604HCID 136400604, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 5-[2-(2-methoxy-phenyl)-thiazol-4-yl]-pentanoic acid methyl ester (3.3 g, 10.8 mmol) in CH2Cl2 (30 mL) under nitrogen at room temperature. Add boron tribromide (1M in CH2Cl2, 27 mL) and stir at room temperature until the reaction is complete. Quench the mixture with methanol, add ice/water and extract with CH2Cl2. Dry the combined extracts over Na2SO4 and concentrate. Chromatograph the resulting residue over silica gel (EtOAc/CH2Cl2) to allow for isolation of 5-[2-(2-hydroxy-phenyl)-thiazol-4-yl]-pentanoic acid methyl ester (2.2 g, 70%). MS (ES): (M+1)+ 292.1 m/z.

Workup

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

Sources & evidence

ORD record
ord-0fa1b23e7bfc40dba73add3ab38141d6
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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