Lithium Carbonate → (E)-[4-(4-bromo-but-2-enyloxy)-2-hydroxy-phenyl]-(4-bromo-phenyl)-methanone

HRID 1636739Notes

Reaction equation

HRID 1636739 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=2[OH:17])=[O:9])=[CH:4][CH:3]=1.[Br:18][CH2:19]/[CH:20]=[CH:21]/[CH2:22]Br.C(=O)([O-])[O-].[Li+].[Li+]>CN(C=O)C>[Br:18][CH2:19]/[CH:20]=[CH:21]/[CH2:22][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)=[O:9])=[C:11]([OH:17])[CH:12]=1

Participants

5

Reactant 3

HCID 11125Lithium CarbonateHCID 641245trans-1,4-Dibromo-2-buteneHCID 11066277(4-Bromo-phenyl)-(2,4-dihydroxyphenyl)-methanone

Product 1

HCID 18434290(E)-[4-(4-bromo-but-2-enyloxy)-2-hydroxy-phenyl]-(4-bromo-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.88 g of (4-bromo-phenyl)-(2,4-dihydroxy-phenyl)-methanone and (E)-1,4-dibromo-2-butene in 7.5 ml of DMF and 0.56 g of lithium carbonate is stirred at 40° C. for 48 hrs. After working up with methylene chloride/0.5M hydrochloric acid and purification over silica gel with hexane/ethyl acetate (9:1) there is obtained 0.14 g of (E)-[4-(4-bromo-but-2-enyloxy)-2-hydroxy-phenyl]-(4-bromo-phenyl)-methanone which, with N-allyl-methyl-amine analogously to Example 3c), gives (E)-[4-(4-allyl-methyl-amino-but-2-enyloxy)-2-hydroxy-phenyl]-(4-bromo-phenyl)-methanone which is converted into the hydrochloride, MS: m/e 416 (M+H+, 1Br).

Workup

  1. customAfter working up with methylene chloride/0.5M hydrochloric acid and purification over silica gel with hexane/ethyl acetate (9:1) there

Sources & evidence

ORD record
ord-0c31728326a24fd3ab4f5bb3348b336f
Source dataset
uspto-grants-2000_03
Patent number
US06034275

Reaction notes

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