Reaction #1833276

Reaction equation

tert-butyl-(trans)-2-(4-hydroxyphenyl)cyclopropylcarbamate

Intermediate N

tert-butyl-(trans)-2-(4-hydroxyphenyl)cyclopropylcarbamate

K2CO3

3-Bromo benzyl bromide

→

tert-butyl(trans)-2-(4-(3-bromobenzyloxy)phenyl)cyclopropylcarbamate

Yield 62.2%

Solvents

DMF

Conditions

Workup

1. 1
   Extractionextracted with EtOAc (2×75 mL)
2. 2
   WashThe combined extracts were washed with water (100 mL), brine (100 mL)
3. 3
   Dryingdried over anhydrous Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated
6. 6
   OtherThe crude residue was purified by flash chromatography

Procedure

To a solution of tert-butyl-(trans)-2-(4-hydroxyphenyl)cyclopropylcarbamate (Intermediate N, 5 g, 20.0 mmol), K2CO3 (6.8 g, 50.0 mmol) in dry DMF (10 vols) was added 3-Bromo benzyl bromide (5 g, 20.0 mmol) and stirred at RT for 16 h. After completion, the reaction mixture was poured into ice water (150 mL) and extracted with EtOAc (2×75 mL). The combined extracts were washed with water (100 mL), brine (100 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by flash chromatography to give (tert-butyl(trans)-2-(4-(3-bromobenzyloxy)phenyl)cyclopropylcarbamate (5.2 g, 62%) as a white solid. The crude was carried to next step without further purification.

Source