N-bromobutanimide → 4-Benzyloxy-3-bromo-1-cyclopentene

HRID 1448992Notes

Reaction equation

[CH2:1]([O:8][CH:9]1[CH2:13][CH:12]=[CH:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:14]N1C(=O)CCC1=O>>[CH2:1]([O:8][CH:9]1[CH2:10][CH:11]=[CH:12][CH:13]1[Br:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 67184N-bromobutanimide

HCID 11788566[(Cyclopent-3-en-1-yloxy)methyl]benzene

Product 1

HCID 203748964-Benzyloxy-3-bromo-1-cyclopentene

Procedure

4-Benzyloxy-1-cyclopentene is brominated with N-bromosuccinimide in the 3-position. The 4-benzyloxy-3-bromo-1-cyclopentene obtained is reacted with 1-heptanol in the presence of silver oxide and the so obtained 4-benzyloxy-3-heptyloxy-1-cyclopentene is epoxidized with m-chloro-perbenzoic acid.

Sources & evidence

ORD record: ord-0e69a0bb191e40369955b1e514611f06
Source dataset: uspto-grants-1980_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04188403

Reaction notes

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