2-Bromo-6H-dibenz[b,e]oxepin-11-one → (Z)-1-[2-(2-Bromo-6,11-dihydrodibenz[b,e]oxepin-11-ylidene)ethyl]pyrrolidine

HRID 1463176Notes

Reaction equation

HRID 1463176 reaction equation
[Br-].[N:2]1([CH2:7][CH2:8][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:6][CH2:5][CH2:4][CH2:3]1.C([Li])CCC.[Br:33][C:34]1[CH:49]=[CH:48][C:37]2[O:38][CH2:39][C:40]3[CH:47]=[CH:46][CH:45]=[CH:44][C:41]=3[C:42](=O)[C:36]=2[CH:35]=1>CCCCCC.O1CCCC1>[Br:33][C:34]1[CH:49]=[CH:48][C:37]2[O:38][CH2:39][C:40]3[CH:47]=[CH:46][CH:45]=[CH:44][C:41]=3/[C:42](=[CH:8]/[CH2:7][N:2]3[CH2:3][CH2:4][CH2:5][CH2:6]3)/[C:36]=2[CH:35]=1

Participants

6

Reactant 3

HCID 129291312-Bromo-6H-dibenz[b,e]oxepin-11-oneHCID 19085441Phosphonium, triphenyl(2-(1-pyrrolidinyl)ethyl)-, bromide (1:1)HCID 178418339Butyllithium

Product 1

HCID 67781199(Z)-1-[2-(2-Bromo-6,11-dihydrodibenz[b,e]oxepin-11-ylidene)ethyl]pyrrolidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Anhydrous 2-(N-pyrrolidinyl)-ethyltriphenylphosphonium bromide (10 g, 45 mmole), 48 mmole of n-butyl lithium in hexane, and 2-bromo-6,11-dihydrodibenz [b,e1-oxepin-11-one (5 g, 35 mmole) were reacted in 300 mL dry tetrahydrofuran by the procedure in Example 1, Step a. This provided the pure Z-isomer (1.76 g) as a light brown solid, mp 108°-109° C.. pmr (DMSO-d6) δ: 7.28-7.50 (m, 6H, aromatic H); 6.80 (d, J=8.8 Hz, 1H, H4); 5.82 (t, 1H, HC=); 5.20 (s, 2H, ArCH2O); 3.29 (m, 2H, NCH2C=); 2.50 (m, 4H, 2NCH2); 1.70 (m, 4H, 2CH2).

Workup

  1. customThis provided the pure Z-isomer (1.76 g) as a light brown solid, mp 108°-109° C.

Sources & evidence

ORD record
ord-0aa12ee51ff84fec98b051bca62cdf0d
Source dataset
uspto-grants-1994_04
Patent number
US05300282

Reaction notes

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