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O3, -78oC
Zn, CH3CO2H

Br2
H2O

Cl2
CH2Cl2

mCPBA

Br2
CH2Cl2

Br2
CH3OH

BH3, THF
NaOH, H2O2, H2O

CH3OH
H2SO4

H2O
H2SO4

HBr

HCl

H2
Pd/C

HBr

2HBr

Br2
CH2Cl2

2Br2

H2O
H2SO4
HgSO4

R2BH, THF
NaOH, H2O2, H2O

2H2
Pd/C

H2
Lindar’s Cat.

Na Or Li
NH3, -78oC