1-(2-Bromoethoxy)-4-fluorobenzene → HCID 44517312, compound

HRID 2192350Notes

Reaction equation

HRID 2192350 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]([C:12]1([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.Br[CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1>C(#N)C>[CH:10]([O-:11])=[O:9].[F:35][C:32]1[CH:33]=[CH:34][C:29]([O:28][CH2:27][CH2:26][N+:1]23[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]2)[C@@H:3]([O:9][C:10]([C:12]2([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH2:2]3)=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 20641711-(2-Bromoethoxy)-4-fluorobenzeneHCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Product 1

HCID 44517312HCID 44517312, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester (Example 14e) (50 mg) and 1-(2-bromoethoxy)-4-fluorobenzene (50 mg) in acetonitrile (1 mL) was stirred at room temperature for 22 h. Purification by prep. HPLC using 5-98% MeCN/H2O containing 0.1% formic acid gave the title compound (19 mg) as a colourless oil.

Workup

  1. customPurification by prep

Sources & evidence

ORD record
ord-a5fe129c8d1749bb9c24fac373b50fe2
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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