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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1643596Generated: October 31, 2026

4-Bromo-2-fluoro-N,N-dimethylbenzamide → 4-(4-Dimethylcarbamoyl-3-fluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

https://huagongshe.com/reaction/1643596

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Bromo-2-fluoro-N,N-dimethylbenzamideHCID 24694297—
ReactantMethyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylateHCID 25067323—
Reactant4-[4-(Azetidine-1-carbonyl)-phenoxy]-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl esterHCID 59560251—
Product4-(4-Dimethylcarbamoyl-3-fluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl esterHCID 59560252—

Reaction Steps

The title compound was prepared in a similar manner as described for Intermediate 35b, from 4-bromo-2-fluoro-N,N-dimethyl-benzamide (589 mg, 2.65 mmol) and 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (3e) (652 mg, 2.65 mmol) to give a white solid (861 mg, 84% yield). 1H NMR (400 MHz, CDCl3) δ 7.33-7.43 (m, 1 H) 7.25 (s, 1 H) 7.22 (s, 1 H) 6.75-6.84 (m, 1 H) 6.66-6.73 (m, 1 H) 3.88 (s, 3 H) 3.13 (s, 3 H) 2.98 (s, 3 H) 2.90 (s, 2 H) 1.49 (s, 6 H); LCMS for C21H22FNO5 m/z 388.00 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08119624B2
Source datasetuspto-grants-2012_02
ORD IDord-14fab9533c034fdf995b53b79f18c0ac
Source noteuspto-grants-2012_02