2-Bromo-5-(trifluoromethyl)benzaldehyde → HCID 57458795, compound

HRID 1810265Notes

Reaction equation

HRID 1810265 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:14][Mg]I>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:6][C:3]=1[CH:4]([OH:5])[CH3:14]

Participants

4

Reactant 2

HCID 70180472-Bromo-5-(trifluoromethyl)benzaldehydeHCID 178418373HCID 178418373, compound

Product 1

HCID 57458795HCID 57458795, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-bromo-5-trifluoromethyl-benzaldehyde (1.0 g, 3.95 mmol) in THF (10 mL) at 0° C. under N2 was added methylmagnesium iodide (3M in diethyl ether; 2.6 mL, 7.91 mmol). The reaction was stirred for 2 hours, and then quenched with saturated aqueous NH4Cl and diluted with CH2Cl2. The aqueous layer was separated and extracted with CH2Cl2, and the combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. additiondiluted with CH2Cl2
  3. customThe aqueous layer was separated
  4. extractionextracted with CH2Cl2
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a00cfb1985bd46b297e0500e4f5c8c45
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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