Ammonium Chloride → 1-(4-Bromo-2-methylphenyl)propan-1-one

HRID 1671355Notes

Reaction equation

HRID 1671355 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[Br:5][C:6]1[CH:17]=[CH:16][C:9]([C:10](N(OC)C)=[O:11])=[C:8]([CH3:18])[CH:7]=1.[Cl-].[NH4+]>C1COCC1>[Br:5][C:6]1[CH:17]=[CH:16][C:9]([C:10](=[O:11])[CH2:1][CH3:2])=[C:8]([CH3:18])[CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 189704854-bromo-N-methoxy-N,2-dimethylbenzamideHCID 178418443HCID 178418443, compound

Product 1

HCID 213363961-(4-Bromo-2-methylphenyl)propan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethylmagnesium bromide (2.35 ml of 3M in diethyl ether, 7.05 mmol) is added slowly to a stirred solution of 4-bromo-N-methoxy-N,2-dimethylbenzamide (0.91 g, 3.53 mmol) in dry THF (40 ml) at 0° C. The reaction is stirred at 0° C. for 1 h followed by RT for 18 h. The reaction mixture is poured into saturated ammonium chloride solution to quench the reaction and concentrated in vacuo to remove most of the THF. The product is extracted with diethyl ether and the combined organic extracts are dried (MgSO4). The solvent is removed in vacuo and the resulting oil is purified by chromatography on silica eluting with iso-hexane:ethyl acetate (3:1) give the title product as a colourless oil. MS m/z 227.0 [M+H]+1H NMR (400 MHz, CDCl3) δ 1.18 (3H, t), 2.45 (3H, s), 2.88 (2H, d), 7.40 (1H, d), 7.43 (1H, s), 7.50 (1H, d).

Workup

  1. waitfollowed by RT for 18 h
  2. customto quench
  3. customthe reaction
  4. concentrationconcentrated in vacuo
  5. customto remove most of the THF
  6. extractionThe product is extracted with diethyl ether
  7. dry with materialthe combined organic extracts are dried (MgSO4)
  8. customThe solvent is removed in vacuo
  9. customthe resulting oil is purified by chromatography on silica eluting with iso-hexane:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-ec8b1182b70e4fa795f41347d8a0c70d
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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