Benzyl Bromide → HCID 22219721, compound

HRID 1614245Notes

Reaction equation

[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:20][CH2:21][CH3:22])(=[O:19])[C:10]1[CH:18]=[CH:17][C:15]([OH:16])=[C:12]([O:13][CH3:14])[CH:11]=1>>[CH2:1]([O:16][C:15]1[CH:17]=[CH:18][C:10]([C:9]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11][C:12]=1[O:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 7498Benzyl Bromide

HCID 12038Ethyl vanillate

Product 1

HCID 22219721HCID 22219721, compoundYield 97%

Procedure

Benzyl bromide was reacted with ethyl vanillate using the conditions described in Example 1 to give ethyl 4-benzyloxy-3-methoxybenzoate in 97% yield m.p. 72°-74° C. Following the procedures described in the portion of Example 6 which is concerned with the preparation of starting materials the product so obtained was reacted with thiazol-2-yl-lithium and the resultant product was reacted with ethylmagnesium iodide to give the required starting material as an oil in 20% yield.

Sources & evidence

ORD record: ord-108238891e9a41c083a6011178d4a8ff
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05196422

Reaction notes

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