HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2085661Generated: November 1, 2026
Dichloromethane → 4-(1H-Indol-6-yl)benzoic acid
https://huagongshe.com/reaction/2085661
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Carboxyphenylboronic Acid | HCID 312183 | — |
| Reactant | 6-Bromoindole | HCID 676493 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-(1H-Indol-6-yl)benzoic acid | HCID 22730381 | — |
Reaction Steps
A mixture of 6-bromoindole (480 mg, 2.45 mmol), 4-(dihydroxyboryl)benzoic acid (406 mg, 2.45 mmol), Pd(dppf)Cl2.CH2Cl2 (10 mg, 0.01 mmol), and 2M Na2CO3 (5.6 mL, 11.2 mmol) in a mixture of ethanol (4 mL) and DMF (7 mL) was heated to 100° C., stirred for 16 hours, filtered, and concentrated. The concentrate was dissolved in ethyl acetate, washed sequentially with 1M H3PO4, water, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 5% methanol/dichloromethane to provide the desired product. MS (ESI(−)) m/e 236 (M−H)−.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06720338B2 |
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| Source dataset | uspto-grants-2004_04 |
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| ORD ID | ord-72e7b12205cb4029ac32ad791793cc9f |
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| Source note | uspto-grants-2004_04 |
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