Hydrogen Bromide → Ethyl 3-(4-(4-bromophenyl)-3-(4-cyano-2-methylphenyl)thiophen-2-yl)propanoate

HRID 536615Notes

Reaction equation

N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][C:21]=3[CH3:28])=[C:10]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[S:11][CH:12]=2)=[CH:4][CH:3]=1.[BrH:29].N([O-])=O.[Na+]>O>[Br:29][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][C:21]=3[CH3:28])=[C:10]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[S:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of ethyl 3-(4-(4-aminophenyl)-3-(4-cyano-2-methylphenyl)thiophen-2-yl)propanoate (180 mg, 0.46 mmol) in a mixture solvent of HBr (48%, 3 mL) and water (1 mL) was added dropwise a solution of NaNO2 (32 mg, 0.46 mmol) in water (0.5 mL). Then the mixture was stirred at 0° C. for 1 hour. Then CuBr (66 mg, 0.46 mmol) was added and the mixture was stirred at 0° C. for additional 1 hour. The reaction mixture was extracted with EtOAc and the combined organic layer was dried over Na2SO4, concentrated in vacuo to give crude ethyl 3-(4-(4-bromophenyl)-3-(4-cyano-2-methylphenyl)thiophen-2-yl)propanoate, which was used in the next step directly.

Workup

stirringthe mixture was stirred at 0° C. for additional 1 hour
extractionThe reaction mixture was extracted with EtOAc
dry with materialthe combined organic layer was dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8c98eeffa3d84eeaa4a1fd54012997b4
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859611B2

Reaction notes

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