Ammonium Chloride → 1-(2-Bromo-6-fluorophenyl)-2-methylpropan-1-one

HRID 1091922Notes

Reaction equation

HRID 1091922 reaction equation
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[Br:6][C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:8]=1[CH:9]=[O:10].[NH4+].[Cl-]>C1COCC1>[Br:6][C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:8]=1[C:9](=[O:10])[CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 224739772-Bromo-6-fluorobenzaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 665895481-(2-Bromo-6-fluorophenyl)-2-methylpropan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Isopropylmagnesium chloride (18 mL of 2 M in Et2O, 35 mmol) is added to a solution of 2-bromo-6-fluoro-benzaldehyde (6.0 g, 30 mmol) in THF (40 mL) at −78° C. and the mixture is stirred for 1 hour at 0° C. The mixture is poured into saturated NH4Cl and extracted with EtOAc. The resulting crude alcohol is oxidized directly by Swem oxidation to yield 1-(2-bromo-6-fluoro-phenyl)-2-methyl-propan-1-one. 1H NMR (CDCl3) 7.38 (d, 1H), 7.22 (m, 1H), 7.03 (t, 1H), 3.10 (m, 1H), 1.11 (d, 6H).

Workup

  1. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-996dc5dde8c649dc8d5e15e4de87212b
Source dataset
uspto-grants-2012_03
Patent number
US08129395B2

Reaction notes

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