4-Fluorobenzyl bromide → HCID 178448138, compound

HRID 1440355Notes

Reaction equation

HRID 1440355 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([Si@H:10]2[CH2:15][CH2:14][C@H:13]([CH2:16]Br)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[Mg].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>[Cu](I)I.C(OP(OCC)(OCC)=O)C.C1COCC1>[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([Si@H:10]2[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:24][C:23]3[CH:26]=[CH:27][C:20]([F:19])=[CH:21][CH:22]=3)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

7

Reactant 3

HCID 680214-Fluorobenzyl bromideHCID 5462224MagnesiumHCID 178448137HCID 178448137, compound

Product 1

HCID 178448138HCID 178448138, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 6535Triethyl PhosphateCatalystHCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

6.3 g (20 mmol) of trans-1-(trans-4-n-propylcyclohexyl)-4-bromomethyl-1-silacyclohexane was dripped into a mixture of 0.5 g (21 mmol) of magnesium and 50 ml of THF to obtain a Grignard's reagent. This solution was then dripped into a 50 ml THF solution of 50 mg of triethylphosphate, 10 mg of copper iodide (I) and 3.9 g (20 mmol) of p-fluorobenzyl bromide. After a conventional after treatment, 6.1 g (yield 85%) of trans-1-(trans-4-n-propylcyclohexyl)-4-(2-(4-fluorophenyl) ethyl)-1-silacyclohexane was obtained.

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-0adfd3434ce24226884ae25c0868a39a
Source dataset
uspto-grants-1996_03
Patent number
US05498737

Reaction notes

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