Tetra-n-butylammonium tribromide → Tert-butyl (1-(4-(2-bromoacetyl)phenyl)cyclobutyl)carbamate

HRID 1046985Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br-:22].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)(Cl)Cl.CO.ClCCl>[Br:22][CH2:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:13][CH2:12][CH2:11]2)=[CH:8][CH:9]=1)=[O:3]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of tert-butyl (1-(4-acetylphenyl)cyclobutyl)carbamate (0.1 g, 1 eq.) in chloroform (3.5 mL) and methanol (1.5 mL) was added the tetrabutyl ammonium tribromide (0.175 g, 1.05 eq.). The mixture was stirred at 40° C. for 90 minutes. The reaction mixture was diluted with dichloromethane (10 mL), washed with water (10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The product was purified by column chromatography (10% ethyl acetate in dichloromethane), giving tert-butyl (1-(4-(2-bromoacetyl)phenyl)cyclobutyl)carbamate (0.1 g, 78%) as a colorless oil. LCMS: 312 [M−tBu+H], 314 [M−tBu+H].

Workup

washwashed with water (10 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe product was purified by column chromatography (10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record: ord-8a0441fe7a0e46158b6fdf4866d02349
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569331B2

Reaction notes

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