2-Bromo-5-chlorothiophene-3-carbaldehyde → 2-Bromo-5-chloro-α-(3-chlorophenyl)-3-thiophenemethanol

HRID 870031Notes

Reaction equation

HRID 870031 reaction equation
[Br:1][C:2]1[S:3][C:4]([Cl:9])=[CH:5][C:6]=1[CH:7]=[O:8].[Cl:10][C:11]1[CH:12]=[C:13]([Mg]Br)[CH:14]=[CH:15][CH:16]=1>C1COCC1.CCOCC>[Br:1][C:2]1[S:3][C:4]([Cl:9])=[CH:5][C:6]=1[CH:7]([C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:10])[CH:16]=1)[OH:8]

Participants

4

Reactant 2

HCID 509991562-Bromo-5-chlorothiophene-3-carbaldehydeHCID 178478127HCID 178478127, compound

Product 1

HCID 451402022-Bromo-5-chloro-α-(3-chlorophenyl)-3-thiophenemethanol

Reagents, catalysts & solvents 1

HCID 21868444Ether tetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-bromo-5-chlorothiophene-3-carbaldehyde from Example 1, Step 3 (2.50 g, 11.1 mmol) in THF/ether at −78° C. was added 3-chlorophenylmagnesium bromide (26.6 mL, 0.5M in THF) in 2 min. and the mixture was stirred at −78° C. for 5 min., quenched with saturated NH4Cl/water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and filtered. The filtrate was concentrated and the residue was purified by flash chromatography (10-20% EtOAc/hexanes) to give the desired product.

Workup

  1. customquenched with saturated NH4Cl/water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by flash chromatography (10-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-985a372f3b59488aa9b448a89e8592f1
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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