3-Methoxyphenol → HCID 23289223, compound

HRID 366440Notes

Reaction equation

HRID 366440 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.Br[C:11]1[S:12][CH:13]=[CH:14][N:15]=1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:9][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 90073-MethoxyphenolHCID 764302-Bromothiazole

Product 1

HCID 23289223HCID 23289223, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methoxyphenol (2.48 g, 20 mmol), 2-bromothiazole (3.28 g, 20 mmol) and Me4N+OH-.5H2O (3.62 g, 20 mmol) were heated in dry DMF (30 mL) under N2 (g) for 16 hours. The mixture was filtered and the filtrate was partitioned between H2O and EtOAc. Organic extracts were pooled, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silica (CHCl3) to yield 2.51 g of 2[(3-methoxyphenyl)oxy]thiazole (GC-MS m/z 207 (M+)). A portion (2.42 g, 11.7 mmol) of this material was dissolved in dry CH2Cl2 (40 mL), and BBr3 (2.2 eq.) was added dropwise at about -10° C. under N2 (g). The mixture was allowed to warm to about 20° C., stirred 3 hours, and then poured into ice/H2O and extracted with CH2Cl2. Organic extracts were washed with 5% NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo to yield 3-[(thiazol-2-yl)oxy]phenol as an oil (1.3 g) which was used without further purification (GC-MS m/z 193 (M+)).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was partitioned between H2O and EtOAc
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica (CHCl3)

Sources & evidence

ORD record
ord-d3bab91fa5e84be3bd1c0dbfe64ac1e3
Source dataset
uspto-grants-2000_10
Patent number
US06130217

Reaction notes

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