4-Fluorobenzyl bromide → HCID 18184955, compound

HRID 1358574Notes

Reaction equation

HRID 1358574 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](C)(O)[C:17]([O:19][CH3:20])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:23][C:24]1[CH:31]=[CH:30][C:27](CBr)=[CH:26][CH:25]=1>[Ag]=O.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH:17]([O:19][CH2:20][C:27]2[CH:30]=[CH:31][C:24]([F:23])=[CH:25][CH:26]=2)[C:6]([O:5][CH3:1])=[O:7])=[CH:14][CH:15]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 680214-Fluorobenzyl bromideHCID 18184970HCID 18184970, compound

Product 1

HCID 18184955HCID 18184955, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 4-(t-butoxycarbonylmethoxy)phenyllactate (3.0 g), 4-fluorobenzylbromide (2.4 ml), silver oxide (9.0 g) and toluene (60 ml) was stirred at 80° C. under a nitrogen atmosphere for 3 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was chromatographed on a silica gel column using hexane:ethyl acetate=5:1 as the eluant to afford the title compound (2.9 g, Rf=0.39: thin layer chromatography on a silica gel plate using hexane:ethyl acetate=3:1 as the eluant).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-f49ef572205d4061ad36d5094da98b9c
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

Loading…