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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1177173Generated: November 1, 2026

4-Bromo-2-chlorobenzonitrile → 4-(3-Chloro-4-cyano-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

https://huagongshe.com/reaction/1177173

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Bromo-2-chlorobenzonitrileHCID 7010420—
ReactantMethyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylateHCID 25067323—
Reactant4-(6-Dimethylcarbamoyl-pyridin-3-yloxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl esterHCID 59560224—
Product4-(3-Chloro-4-cyano-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl esterHCID 66755856—

Reaction Steps

The title compound was prepared in a similar manner as described for Intermediate 161b, from 4-bromo-2-chlorobenzonitrile (292 mg, 1.35 mmol) and 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (3e) (300 mg, 1.35 mmol) to give a white foam (116 mg, 24% yield). 1H NMR (400 MHz, CDCl3) δ 7.62 (d, J=8.59 Hz, 1 H) 7.25-7.34 (m, 1 H) 7.23 (d, J=1.01 Hz, 1 H) 7.04 (d, J=2.27 Hz, 1 H) 6.90 (dd, J=8.72, 2.40 Hz, 1 H) 3.88 (s, 3 H) 2.87 (s, 2 H) 1.48 (s, 6 H); LCMS for C19H16ClNO4 m/z 380.00 (M+Na+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07842713B2
Source datasetuspto-grants-2010_11
ORD IDord-39f8b85900be42a193b28e32e0894c7e
Source noteuspto-grants-2010_11