Benzene → 6-bromo-1H-indene

HRID 42678

Reaction equation

HRID 42678 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=O)[CH2:6][CH2:5]2.[BH4-].[Na+].S(=O)(=O)(O)O.C1C=CC=CC=1>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8]([CH:7]=[CH:6][CH2:5]2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 1118Sulfuric AcidHCID 5206955-Bromo-1-indanoneHCID 4311764Sodium borohydride

Product 1

HCID 126795186-bromo-1H-indene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Sources & evidence

ORD record
ord-0d8eca445b2e4f0ea9bc68a2e4bf60e2
Source dataset
uspto-grants-2013_09
Patent number
US08536189B2

Linked notes

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