3-Bromo-2-fluorobenzaldehyde → (3-Bromo-2-fluorophenyl)(phenyl)methanol

HRID 871124Notes

Reaction equation

HRID 871124 reaction equation
[Br:1][C:2]1[C:3]([F:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[C:11]1([Mg]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[Br:1][C:2]1[C:3]([F:10])=[C:4]([CH:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:6])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 220193613-Bromo-2-fluorobenzaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 71743205(3-Bromo-2-fluorophenyl)(phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-bromo-2-fluorobenzaldehyde (0.150 g, 0.739 mmol) in THF (3.21 mL) cooled to −78° C. was added phenylmagnesium bromide (0.887 mL, 0.887 mmol). The reaction mixture was maintained at −78° C. for at least 1 hr and then allowed to warm to room temperature slowly over 3 hr. The reaction was quenched with a saturated aqueous solution of NH4Cl. The reaction mixture was diluted with CH2Cl2 and the layers were separated. The aqueous phase was extracted twice with CH2Cl2. The organic layers were combined, dried over Na2SO4, filtered, and concentrated to afford the title compound as a colorless residue.

Workup

  1. temperatureto warm to room temperature slowly over 3 hr
  2. customThe reaction was quenched with a saturated aqueous solution of NH4Cl
  3. additionThe reaction mixture was diluted with CH2Cl2
  4. customthe layers were separated
  5. extractionThe aqueous phase was extracted twice with CH2Cl2
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cdc94b3ba03c4bd78911e3a632065075
Source dataset
uspto-grants-2015_03
Patent number
US08969586B2

Reaction notes

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