1,1-Dibromoethane → HCID 69033169, compound

HRID 1868610Notes

Reaction equation

HRID 1868610 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:24])[CH:7]=[C:8]([C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)[O:9]2)=[CH:4][CH:3]=1.[Br:25][CH:26](Br)[CH3:27].C(=O)([O-])[O-].[K+].[K+].[K+].[Br-]>CN(C)C=O>[Br:25][CH2:26][CH2:27][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:24])[CH:7]=[C:8]([C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)[O:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 112011,1-DibromoethaneHCID 11430Potassium CarbonateHCID 253877Potassium BromideHCID 53819207-Hydroxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one2×

Product 1

HCID 69033169HCID 69033169, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound (58) was prepared from 7-hydroxy-3′,4′,5′-trimethoxy-flavone, 25 (2.3 g, 7 mmol), dibromo ethane (3 mL, 35 mmol) and potassium carbonate (2.9 g, 21 mmol) in dry dimethyl formamide (120 mL) using the identical procedure as described for 56. Yield 2.1 g (68%); mp 184-185° C.; MS (FAB) 435/437 (M++1); IR (KBr) 1631; 1H NMR (200 MHz, CDCl3) δ 8.15 (d, J=9.3 Hz, 1H), 7.10 (s, 2H), 7.01 (d, J=7.8 Hz, 1H), 6.99 (s, 1H), 6.71 (s, 1H), 4.43 (t, J=6.2 Hz, 2H), 3.96 (s, 6H), 3.93 (s, 3H), 3.70 (t, J=6.2 Hz, 2H).

Sources & evidence

ORD record
ord-bd1a01de0b2b4f1db115b03b2bc21d40
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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