Hydrochloric Acid → 6-Bromo-benzo[b]thiophene

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	1,8-Diazabicyclo(5.4.0)undec-7-ene	HCID 81184	—
Reactant	6-Bromo-1-benzothiophene-2-carboxylic acid	HCID 13567980	—
Solvent	Hexane	HCID 8058	—
Solvent	Dimethylacetamide	HCID 31374	—
Product	6-Bromo-benzo[b]thiophene	HCID 12744400	78%

Reaction Conditions

Temperature	200 °C

Reaction Steps

DBU (1.21 g, 8.00 mmol) was added to a stirred solution of 6-bromo-benzo[b]thiophene-2-carboxylic acid (I-25b: 2.4 g, 8.85 mmol) in DMA (4 mL) at room temperature and the resulting mixture was heated in microwave at 200° C. for 1 hour. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mixture was acidified with 1N HCl and extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography on silica gel (100% hexane) to afford 320 mg of the product (78% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09339501B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-786e68a5ac7e44a9b303b49a6c676aac
Source note	uspto-grants-2016_05