1,2-Dibromoethane → 1-(2-Bromoethoxy)-4-[2-(tertiary butoxycarbonylamino)-2-methylpropoxy]-benzene

HRID 620086Notes

Reaction equation

HRID 620086 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:20])([CH3:19])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:27][CH2:28][CH2:29]Br>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[Br:27][CH2:28][CH2:29][O:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][CH2:10][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])([CH3:20])[CH3:19])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 54328448p-[2-(Tertiary butoxycarbonylamino)-2-methylpropoxy]-phenol

Product 1

HCID 212484381-(2-Bromoethoxy)-4-[2-(tertiary butoxycarbonylamino)-2-methylpropoxy]-benzene

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

Analogously to Example (2b), a mixture of 19.2 g (68 mmol) of p-[2-(tertiary butoxycarbonylamino)-2-methylpropoxy]-phenol, 47 g (340 mmol) of potassium carbonate and 1.5 g of triethylbenzylammonium chloride is reacted in 57 ml (680 mmol) of 1,2-dibromoethane and worked up. Crude 1-(2-bromoethoxy)-4-[2-(tertiary butoxycarbonylamino)-2-methylpropoxy]-benzene is obtained in the form of an oil, which is used further in crude form.

Sources & evidence

ORD record
ord-74502b05368e48e2914891a1fe07cd7d
Source dataset
uspto-grants-1989_04
Patent number
US04818766

Reaction notes

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