Boron tribromide → HCID 136400604, compound

HRID 1616635Notes

Reaction equation

HRID 1616635 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-4b3a8300d0b14cee9c2e97ed8c82e49a
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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