Reaktion #70956

ord-0d8eca445b2e4f0ea9bc68a2e4bf60e2

Reaktionsgleichung

O=S(=O)(O)O
sulfuric acid
O=C1CCc2cc(Br)ccc21
5-bromo-1-indanone
[BH4-].[Na+]
sodium borohydride
c1ccccc1
benzene
Brc1ccc2c(c1)CC=C2
6-bromo-1H-indene

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Reduction of 5-bromo-1-indanone E1 with sodium borohydride in MeOH followed by dehydration of the resulting alcohol with sulfuric acid in refluxing benzene at about 80° C. affords 6-bromo-1H-indene E2 (CAS#33065-61-1; see, Young J R, Huang S X, Walsh T F, Wyvratt M J, Yang Y T, Yudkovitz J B, Cui J, Mount G R, Ren R N, Wu T-J, Shen X, Lyons K A, Mao A-H, Carlin J R, Karanam B V, Vincent S H, Cheng K and Goulet M T, Bioorg. Med. Chem. Lett. 2002, 12 (5), 827-832).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536189B2uspto-grants-2013_09