2-Bromothiazole → HCID 23289316, compound

HRID 366439Notes

Reaction equation

HRID 366439 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:17]1[S:18][CH:19]=[CH:20][N:21]=1>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:17]1[S:18][CH:19]=[CH:20][N:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 764302-BromothiazoleHCID 804592-Benzyloxyphenol

Product 1

HCID 23289316HCID 23289316, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

o-Benzyloxyphenol (7.5 g, 37.5 mmol) in dry DMF (60 mL) was treated with Me4N+OH-.5H2O (37.5 mmol, 6.8 g) followed by 2-bromothiazole (6.15 g, 37.5 mmol). The stirred solution was heated to about 100° C. under N2 (g) for 16 hours. The mixture was cooled in ice and crystalline, H2O-soluble Me4N+Br- was removed by filtration. The filtrate was concentrated in vacuo and partitioned between Et2O (100 mL) and H2O (60 mL). The organic phase was washed with 1N NaOH (3×) and brine, dried over Na2SO4 and concentrated in vacuo to afford 4.9 g of crude 2-(2-benzyloxyphenyl)thiazole (GCMS m/z 283 (M+)). This material was directly deprotected by treatment with 33% HBr in HOAc (35 mL) for 2 hours at about 20° C.

Workup

  1. temperatureThe mixture was cooled in ice
  2. customcrystalline, H2O-soluble Me4N+Br- was removed by filtration
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompartitioned between Et2O (100 mL) and H2O (60 mL)
  5. washThe organic phase was washed with 1N NaOH (3×) and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b1771c7c193346fa839da4ae35ad19b2
Source dataset
uspto-grants-2000_10
Patent number
US06130217

Reaction notes

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