Ammonium Chloride → HCID 58579838, compound

HRID 2059871Notes

Reaction equation

HRID 2059871 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][C:8](N(OC)C)=[O:9])=[C:4]([O:16][CH3:17])[CH:3]=1.[CH:18]1([Mg]Br)[CH2:20][CH2:19]1.[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][C:8]([CH:18]2[CH2:20][CH2:19]2)=[O:9])=[C:4]([O:16][CH3:17])[CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 58579883HCID 58579883, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 58579838HCID 58579838, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-bromo-2-methoxyphenoxy)-N-methoxy-N-methylacetamide Part A (2 g, 6.58 mmol) in THF (25 mL) was slowly added cyclopropylmagnesium bromide (39.5 mL, 19.73 mmol). After stirring for 1 hour at RT, the reaction mixture was added to a sat. NH4Cl solution which was subsequently extracted with EtOAc, dried (Na2SO4), and concentrated. The crude product was purified using ISCO flash chromatography (silica gel/hexanes-ethyl acetate 100:0 to 50:50 gradient) to afford the desired product 2-(4-bromo-2-methoxyphenoxy)-1-cyclopropylethanone 16B (1.72 g, 6.03 mmol, 92% yield) as a yellow oil. 1H NMR (400 MHz, chloroform-d) δ 7.01 (2H, dddd), 6.65 (1H, d, J=8.53 Hz), 4.72 (2H, s), 3.89 (3H, s), 2.24-2.35 (1H, m), 1.15 (2H, quin, J=3.83 Hz), 0.98 (2H, dq, J=7.56, 3.67 Hz).

Workup

  1. extractionwas subsequently extracted with EtOAc
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-2f74c527d13e438cb39b243335aeeb40
Source dataset
uspto-grants-2012_10
Patent number
US08278316B2

Reaction notes

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