Bromine → ethyl (2Z)-4-bromo-2-[(1R,2S)-2-methylcyclohexyl]oxyimino-3-oxobutanoate

HRID 1194916Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[O:8]/[N:9]=[C:10](/[C:16](=[O:18])[CH3:17])\[C:11]([O:13][CH2:14][CH3:15])=[O:12].[Br:19]Br>>[Br:19][CH2:17][C:16](=[O:18])/[C:10](=[N:9]/[O:8][C@@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C@@H:2]1[CH3:1])/[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

Reactant 2

HCID 24408Bromine

HCID 140352859ethyl (2Z)-2-[(1R,2S)-2-methylcyclohexyl]oxyimino-3-oxobutanoate

Product 1

HCID 88627782ethyl (2Z)-4-bromo-2-[(1R,2S)-2-methylcyclohexyl]oxyimino-3-oxobutanoateYield 68%

Procedure

Ethyl (Z)-2-(cis-2-methylcyclohexyloxyimino)-3-oxobutyrate (0.46 g) was treated with bromine as described in Example 4c to give the title compound (0.41 g, 68%), νmax (film) 2930, 1740, and 1695 cm-1, δH (CDCl3) 0.95 (3H, d, J 6.7 Hz), 1.35 (3H, t), 1.3-2.1 (9H, m), 4.35 (2H, s), 4.38 (2H, q), and 4.40 (1H, m). [Mass spectrum: +ve ion (ammonia) MH+ (334)].

Sources & evidence

ORD record: ord-545d20cee26c404b96553fcaf99648f2
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04816452

Reaction notes

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