Methyl 2,5-dibromopentanoate → Methyl 5-bromo-2-(5-ethoxycarbonyl-2-nitrophenoxy)valerate

HRID 414063Notes

Reaction equation

HRID 414063 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH:17]([CH2:22][CH2:23][CH2:24][Br:25])[C:18]([O:20][CH3:21])=[O:19]>>[Br:25][CH2:24][CH2:23][CH2:22][CH:17]([O:1][C:2]1[CH:3]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:18]([O:20][CH3:21])=[O:19]

Participants

3

Reactant 2

HCID 10912698Methyl 2,5-dibromopentanoateHCID 12784564Ethyl 3-hydroxy-4-nitrobenzoate

Product 1

HCID 21282570Methyl 5-bromo-2-(5-ethoxycarbonyl-2-nitrophenoxy)valerate

Procedure

By a process similar to that of Reference Example 5, ethyl 3-hydroxy-4-nitrobenzoate was allowed to react with methyl 2,5-dibromovalerate to give methyl 5-bromo-2-(5-ethoxycarbonyl-2-nitrophenoxy)valerate as an oily product (yield: 80.2%). This product was subjected to catalytic reduction to obtain ethyl 2-(3-bromopropyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-7-carboxylate, m.p. 118°-119° C. The yield was 90.7%.

Sources & evidence

ORD record
ord-9561cb3d8cf341caa58fde33fdac3c70
Source dataset
uspto-grants-1988_12
Patent number
US04789675

Reaction notes

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