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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1469720Generated: November 1, 2026

Pivaloyl chloride → Methyl 2-chloro-5-(pivalamidomethyl)benzoate

https://huagongshe.com/reaction/1469720

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPivaloyl chlorideHCID 62493—
ReactantDiisopropylethylamineHCID 81531—
ReactantMethyl 5-(aminomethyl)-2-chlorobenzoate--hydrogen chloride (1/1)HCID 66524840—
SolventTetrahydrofuranHCID 8028—
ProductMethyl 2-chloro-5-(pivalamidomethyl)benzoateHCID 67971274117.5%

Reaction Steps

The title compound was prepared following the procedure described in step-2 of Intermediate-2 using methyl 5-(aminomethyl)-2-chlorobenzoate hydrochloride (1.80 g, 6.00 mmol), DIPEA (3.096 g, 2.4 mmol) and pivaloyl chloride (1.2 mL, 9.0 mmol) in THF (20 mL) to afford 2.0 g of the title product. 1H NMR (300 MHz, DMSO d6): 8.16 (m, 1H), 7.65 (s, 1H), 7.53 (d, J=8.4 Hz, 1H), 7.41 (d, J=8.4 Hz, 1H), 4.25 (d, J=5.7 Hz, 2H), 3.85 (s, 3H), 1.15 (s, 9H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09006257B2
Source datasetuspto-grants-2015_04
ORD IDord-c7f92b8771ea4b50b7d66da2f6c25668
Source noteuspto-grants-2015_04