3a,4,5,7a-Tetrahydro-2-benzofuran-1,3-dione → N-(4-bromo-2-fluoro-5-ethoxymethylphenyl)-3,4,5,6-tetrahydrophthalimide

HRID 231450Notes

Reaction equation

HRID 231450 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([NH2:13])=[CH:8][C:3]=1[CH2:4][O:5][CH2:6][CH3:7].[C:14]1(=O)[O:19][C:17](=[O:18])[CH:16]2[CH2:20][CH2:21][CH:22]=[CH:23][CH:15]12>C(O)(=O)C>[Br:1][C:2]1[C:3]([CH2:4][O:5][CH2:6][CH3:7])=[CH:8][C:9]([N:13]2[C:17](=[O:18])[C:16]3[CH2:20][CH2:21][CH2:22][CH2:23][C:15]=3[C:14]2=[O:19])=[C:10]([F:12])[CH:11]=1

Participants

4

Reactant 2

HCID 127266013a,4,5,7a-Tetrahydro-2-benzofuran-1,3-dioneHCID 20032368Ethyl 2-bromo-4-fluoro-5-aminobenzyl ether

Product 1

HCID 14501845N-(4-bromo-2-fluoro-5-ethoxymethylphenyl)-3,4,5,6-tetrahydrophthalimideYield 40.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

By the method of Example 2, Step H, 1.61 g (0.00649 mole) of ethyl 2-bromo-4-fluoro-5-aminobenzyl ether and 1.08 g (0.0071 mole) of tetrahydrophthalic anhydride were reacted in 30 ml of glacial acetic acid, yielding 1.01 g of N-(4-bromo-2-fluoro-5-ethoxymethylphenyl)-3,4,5,6-tetrahydrophthalimide as a yellow solid, m.p. 104°-106° C. The nmr and ir spectra were consistent with the proposed structure.

Sources & evidence

ORD record
ord-b1c6f85c5cc34adcb093b2b0bfe1a76d
Source dataset
uspto-grants-1989_07
Patent number
US04846882

Reaction notes

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