Ammonium Chloride → HCID 22039831, compound

HRID 1016803Notes

Reaction equation

HRID 1016803 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[Mg].C1(Br)CC1.[CH2:11]([C:13]1[CH:18]=[C:17](I)[CH:16]=[CH:15][C:14]=1[O:20][CH2:21][O:22][CH3:23])[CH3:12].[Cl-].[NH4+]>C1COCC1.C1(C)C=CC=CC=1>[CH:1]1([C:17]2[CH:16]=[CH:15][C:14]([O:20][CH2:21][O:22][CH3:23])=[C:13]([CH2:11][CH3:12])[CH:18]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 78037BromocyclopropaneHCID 5462224MagnesiumHCID 22038990HCID 22038990, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 22039831HCID 22039831, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of cyclopropylmagnesium bromide, freshly prepared from 2.49 g of magnesium and 13.3 g of cyclopropyl bromide in 40 ml of THF, was treated with 1.2 g of bistriphenyl-phosphine-nickel chloride and at 35-45° C. within 20 minutes with a solution of 20.8 g of 2-ethyl-4-iodo-1-methoxymethoxy-benzene in 40 ml of toluene. After stirring for 2 hours the reaction mixture was poured into aqueous ammonium chloride solution and extracted with ether. The organic phases were washed with water, saturated aqueous sodium bicarbonate solution and sodium chloride solution, dried over magnesium sulphate and concentrated. The residue was chromatographed over silica gel and gave 12.7 g of 4-cyclopropyl-2-ethyl-1-methoxymethoxy-benzene; MS (EI) m/z 206 (M), 176 (M−CH2O).

Workup

  1. extractionextracted with ether
  2. washThe organic phases were washed with water, saturated aqueous sodium bicarbonate solution and sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-0426e214217143efbfbf78394bc8b557
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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