Hydrogen Bromide → HCID 19009259, compound

HRID 1742489Notes

Reaction equation

[C:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:15][C:16](=[O:18])[CH3:17])=[C:7]([Cl:19])[C:6]=1[O:20][C:21]1[CH:26]=[CH:25][C:24](N)=[CH:23][CH:22]=1)(=[O:3])[CH3:2].[BrH:28].[N+]([O-])([O-])=O.[Na+].[C:34]([O:38][CH2:39][CH2:40][CH2:41][CH3:42])(=[O:37])[CH:35]=[CH2:36]>>[Br:28][CH:35]([CH2:36][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:6]2[C:7]([Cl:19])=[C:8]([O:15][C:16](=[O:18])[CH3:17])[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5]=2[O:4][C:1](=[O:3])[CH3:2])=[CH:22][CH:23]=1)[C:34]([O:38][CH2:39][CH2:40][CH2:41][CH3:42])=[O:37]

Participants

Reactant 4

HCID 260Hydrogen Bromide

HCID 8846Butyl Acrylate

HCID 24268Sodium Nitrate

HCID 19009249HCID 19009249, compound

Product 1

HCID 19009259HCID 19009259, compound

Procedure

Following a procedure similar to that described in Preparation 1(d), 8.3 g of 1,4-diacetoxy-2-(4-aminophenoxy)-3-chloronaphthalene [prepared as described in step (c) above] were arylated using 15 g of a 47% w/v aqueous solution of hydrobromic acid, 1.9 g of sodium nitrate, 27 g of butyl acrylate and 0.5 g of cupric bromide, to give 5.8 g of the title compound as a pale yellow oil.

Sources & evidence

ORD record: ord-a2ffb4074ffd49549b9afd655a5a4b06
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05338855

Reaction notes

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