Benzyl chloroformate → benzyl N-(2-bromoethyl)carbamate

HRID 1873970Notes

Reaction equation

O1CCOCC1.[CH2:7]([O:14][C:15](Cl)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br.[Br:19][CH2:20][CH2:21][NH2:22].O1CCOCC1.[OH-].[Na+]>C(OCC)(=O)C.O>[Br:19][CH2:20][CH2:21][NH:22][C:15](=[O:16])[O:14][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 1,4-dioxane (50 mL) solution comprising benzylchloroformate (17.5729 g; manufactured by Wako Pure Chemical Industries, Ltd.), an aqueous solution of 2-bromoethane amine hydrogen bromide salt-1,4-dioxane [104 mL; solution which was prepared by dissolving 2-bromoethane amine hydrogen bromide salt (21.3617 g; manufactured by Tokyo Chemical Industry, Co., Ltd.) in water (54 mL) and 1,4-dioxane (54 mL)] and an aqueous solution of 2 mol/L-sodium hydroxide (104 mL; manufactured by Kanto Chemical Co., Inc.) were added dropwise simultaneously, and stirred at 0° C. for 2 hours. The reaction solution was added with water and extraction was carried out twice with ethyl acetate. The organic layer was washed twice with saturated sodium hydride, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=94:6→73:27) to obtain the title compound (19.2014 g).

Workup

washThe organic layer was washed twice with saturated sodium hydride
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=94:6→73:27)

Sources & evidence

ORD record: ord-d0b0d6f6e55b46a7acd82705f088de0a
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304443B2

Reaction notes

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