1,2-Dibromoethane → HCID 178443368, compound

HRID 1461129Notes

Reaction equation

HRID 1461129 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH2:3][CH2:4]Br.[Mg:12].C(Br)C[Br:15].[Cl-].CC(CCCC(C)C)CC[Zn+].C(OC(C)(CCC(Cl)C(=C)C)C=C)(=O)C>[Cl-].[Zn+2].[Cl-].O1CCCC1>[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])[CH2:3][CH2:4][Mg:12][Br:15]

Participants

8

Reactant 5

HCID 78391,2-DibromoethaneHCID 1379141-Bromo-3,7-dimethyloctaneHCID 5462224MagnesiumHCID 111605936-Chloro-7-methylene-3-methyl-1-octen-3-yl acetateHCID 178443371HCID 178443371, compound

Product 1

HCID 178443368HCID 178443368, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

In a similar manner to that described in Example 1, a tetrahydrofuran solution of 3,7-dimethyloctylmagnesium bromide was prepared from 6.64 g (0.03 mol) of 3,7-dimethyloctyl bromide, 0.73 g of metallic magnesium, 40 ml of tetrahydrofuran and 3 droplets of ethylene bromide and converted into a tetrahydrofuran solution of 3,7-dimethyloctylzinc chloride by the addition of 4.08 g (0.03 mol) of anhydrous zinc chloride. The subsequent step was conducted with this solution, 0.2 g (0.001 mol) of CuBr·(CH3)2S and 4.4 g (0.02 mol) of 6-chloro-7-methylene-3-methyl-1-octen-3-yl acetate in a similar manner to that described in Example 20 to give 4.1 g of the objective compound as a colorless liquid (yield: 61.2%).

Sources & evidence

ORD record
ord-de217d34892e4e7e9c4ee530ba481659
Source dataset
uspto-grants-1991_12
Patent number
US05073659

Reaction notes

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