1,1-Dibromoethane → HCID 69032853, compound

HRID 1868609Notes

Reaction equation

HRID 1868609 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:12]1[O:13][C:14]2[C:19]([C:20](=[O:22])[CH:21]=1)=[CH:18][CH:17]=[C:16]([OH:23])[CH:15]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:35][CH:36](Br)[CH3:37].C(=O)([O-])[O-].[K+].[K+].[K+].[Br-]>CN(C)C=O>[Br:35][CH2:36][CH2:37][O:23][C:16]1[CH:15]=[C:14]2[C:19]([C:20](=[O:22])[CH:21]=[C:12]([C:11]3[CH:24]=[CH:25][C:26]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:10]=3)[O:13]2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 112011,1-DibromoethaneHCID 11430Potassium CarbonateHCID 253877Potassium BromideHCID 10575539HCID 10575539, compound2×

Product 1

HCID 69032853HCID 69032853, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound (57) was prepared from 3′,4′-dibenzyloxy-7-hydroxy-flavone, 23 (2.3 g, 5.1 mmol), dibromo ethane (1.7 mL, 20.4 mmol) and potassium carbonate (3.5 g, 25.5 mmol) in dry dimethyl formamide (90 mL) using the identical procedure as described for 56. Yield 2.1 g (74%); mp 167-168° C.; MS (FAB) 557/559 (M++1); IR (KBr) 1626; 1H NMR (200 MHz, CDCl3) δ 8.12 (d, J=8.8 Hz, 1H), 7.50-7.32 (m, 12H), 7.01 (d, J=9.1 Hz, 1H), 6.92 (dd, J=8.9 Hz, 2.2 Hz, 1H), 6.91 (s, 1H), 6.60 (s, 1H), 5.24 (s, 4H), 4.39 (t, J=6.2 Hz, 2H), 3.69 (t, J=6.3 Hz, 2H).

Sources & evidence

ORD record
ord-555a6ef761fc411dbb3d31f23b8dc209
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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