HCID 21692926, compound → HCID 66915422, compound

HRID 449137Notes

Reaction equation

HRID 449137 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:4][C:3]=1[F:16].[CH3:17][Mg]Br>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([OH:9])[CH3:17])=[CH:4][C:3]=1[F:16]

Participants

4

Reactant 2

HCID 21692926HCID 21692926, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 66915422HCID 66915422, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of (4-bromo-3-fluorophenyl)-phenylmethanone (200 mg, 0.717 mmol) in THF (6 mL) was added 1.4 M of methylmagnesium bromide in THF (1.8 mL, 2.5 mmol) slowly at −78° C. The reaction was stirred at −78° C. for 4 h. The reaction was quenched with sat. aq. NaHCO3 at −78° C. The crude material was extracted with DCM and concentrated in vacuo to afford the title compound as a colorless oil which was used for next step without further purification.

Workup

  1. customThe reaction was quenched with sat. aq. NaHCO3 at −78° C
  2. extractionThe crude material was extracted with DCM
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-385e4e6904b04252854ce50e44bc780b
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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