2-Bromothiazole → (3-Bromo-2-fluorophenyl)(thiazol-2-yl)methanol

HRID 871131Notes

Reaction equation

HRID 871131 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C([Mg]Cl)(C)C.[Br:12][C:13]1[C:14]([F:21])=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17]>C1COCC1>[Br:12][C:13]1[C:14]([F:21])=[C:15]([CH:16]([C:2]2[S:3][CH:4]=[CH:5][N:6]=2)[OH:17])[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 764302-BromothiazoleHCID 220193613-Bromo-2-fluorobenzaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 86730392(3-Bromo-2-fluorophenyl)(thiazol-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromothiazole (0.088 mL, 0.985 mmol) in THF (2.99 mL) cooled to 0° C. was added isopropylmagnesium chloride (0.493 mL, 0.985 mmol). After 50 min, 3-bromo-2-fluorobenzaldehyde (0.200 g, 0.985 mmol) was added. The reaction mixture was allowed to warm to room temperature overnight. After 12 hr, the reaction was quenched with saturated aqueous NH4Cl. The reaction mixture was diluted with CH2Cl2. The layers were separated. The aqueous phase was extracted with CH2Cl2 (2×). The organic phases were combined, dried over Na2SO4, filtered, and concentrated to afford the title compound as a brown liquid.

Workup

  1. waitAfter 12 hr
  2. customthe reaction was quenched with saturated aqueous NH4Cl
  3. additionThe reaction mixture was diluted with CH2Cl2
  4. customThe layers were separated
  5. extractionThe aqueous phase was extracted with CH2Cl2 (2×)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6212d96390894a2488576604565032f9
Source dataset
uspto-grants-2015_03
Patent number
US08969586B2

Reaction notes

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