Hydrochloric Acid → HCID 44554577, compound

HRID 1749743Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[CH:3]=1.[Br:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[C:16]2[CH:22]=O.Cl>C(O)C>[Br:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[C:16]2/[CH:22]=[C:7]1\[O:8][C:4]2[CH:3]=[C:2]([OH:1])[CH:11]=[CH:10][C:5]=2[C:6]\1=[O:9]

Participants

Conditions

Temperature: 75 °C

Procedure

A solution of 6-hydroxybenzofuran-3(2H)-one (0.50 g, 3.3 mmol) and 5-bromo-1H-indole-3-carboxaldehyde (0.90 g, 4.0 mmol) in ethanol (10 mL) was added with concentrated hydrochloric acid (1.0 mL), and the mixture was stirred at 75° C. for 2 hours. The reaction mixture was cooled to room temperature, and then the solid was collected by filtration, and washed with methanol to obtain (Z)-2-[(5-bromo-1H-indol-3-yl)methylene]-6-hydroxybenzofuran-3(2H)-one (1.1 g, 95%).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationthe solid was collected by filtration
washwashed with methanol

Sources & evidence

ORD record: ord-8de33814ac454e6780cd6775c16a5728
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156827B2

Reaction notes

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