Ammonium Chloride → 1-[2-(4-Bromo-2-methyl-phenyl)-thiazol-5-yl]-ethanol

HRID 41672Notes

Reaction equation

HRID 41672 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH:13]=[O:14])=[CH:11][N:12]=2)=[C:4]([CH3:15])[CH:3]=1.[CH3:16][Mg+].[Br-].[NH4+].[Cl-]>CCOCC.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH:13]([OH:14])[CH3:16])=[CH:11][N:12]=2)=[C:4]([CH3:15])[CH:3]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 595846212-(4-Bromo-2-methyl-phenyl)-thiazole-5-carbaldehydeHCID 178418689HCID 178418689, compound

Product 1

HCID 595846761-[2-(4-Bromo-2-methyl-phenyl)-thiazol-5-yl]-ethanolYield 70.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of 2-(4-bromo-2-methyl-phenyl)-thiazole-5-carbaldehyde (1.9 g, 6.7 mmol) in ether at 0° C. is treated with 3.0 M MeMgBr (5 ml, 15 mmol) in diethyl ether (50 ml). The reaction mixture is stirred for 2 hours then carefully diluted with water. Acidified with aq. sat. NH4Cl. The aqueous layer is extracted with DCM (2×100 ml). The combined organic layers are dried over magnesium sulphate, filtered and evaporated to dryness to give 1.80 g of crude product. The crude product is purified by flash chromatography on silica gel to give 1-[2-(4-bromo-2-methyl-phenyl)-thiazol-5-yl]-ethanol (1.40 g).

Workup

  1. extractionThe aqueous layer is extracted with DCM (2×100 ml)
  2. dry with materialThe combined organic layers are dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customto give 1.80 g of crude product
  6. customThe crude product is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-4e402bfbafc24c3bbd8d970403719046
Source dataset
uspto-grants-2013_09
Patent number
US08530667B2

Reaction notes

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