4-Bromo-6,11-dihydrodibenz[b,e]oxepin-11-one → (Z)-1-[2-(4-Bromo-6,11-dihydrodibenz[b,e]oxepin-11-ylidene)-ethyl]pyrrolidine

HRID 1463181Notes

Reaction equation

HRID 1463181 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[C:39]2[O:40][CH2:41][C:42]3[CH:49]=[CH:48][CH:47]=[CH:46][C:43]=3[C:44](=O)[C:38]=2[CH:37]=[CH:36][CH:35]=1>CCCCCC.O1CCCC1>[Br:33][C:34]1[C:39]2[O:40][CH2:41][C:42]3[CH:49]=[CH:48][CH:47]=[CH:46][C:43]=3/[C:44](=[CH:8]/[CH2:7][N:2]3[CH2:3][CH2:4][CH2:5][CH2:6]3)/[C:38]=2[CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 151138354-Bromo-6,11-dihydrodibenz[b,e]oxepin-11-oneHCID 19085441Phosphonium, triphenyl(2-(1-pyrrolidinyl)ethyl)-, bromide (1:1)HCID 178418339Butyllithium

Product 1

HCID 67803593(Z)-1-[2-(4-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 (20 g, 45 mmole), 45 mmole of n-butyl lithium in hexane (1.6 M), and 4-bromo-6,11-dihydrodibenz[b,e]oxepin-11-one (10 g, 35 mmole) were reacted in 550 mL dry tetrahydrofuran by the procedure in Example 1, Step a. This offered a (Z)/(E) (60:40) isomeric product as a light brown oil. pmr (DMSO-d6)δ: 7.28-7.56 (m, 5H, aromatic H); 7.15-7.26 (2 dd, 1H, H1); 6.88 (t, H3 of 60% Z); 6.84 (t, H3 of 40% E); 6.16 (t, CH= of 40% E): 5.86 (t, CH= of 60% Z); 5.30 (br s, 2H, ArCH2O); 2.28-2.54 (m, 6H, N(CH2)3); 1.66 (m, 4H, 2CH2).

Sources & evidence

ORD record
ord-97d6a4201f2a489887b200fc163be197
Source dataset
uspto-grants-1994_04
Patent number
US05300282

Reaction notes

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