N-bromobutanimide → 1,1-Dimethylethyl N-(1-bromo-2-naphthalenyl)carbamate

HRID 2238367Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].C1C(=O)N([Br:26])C(=O)C1>CC#N>[Br:26][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of tert-butyl 2-naphthylcarbamate (104) [PCT Int. Appl. (2002) WO 02/067930, Searcey, M., Patterson, L. H.] (20.3 g, 83 mmol) in MeCN (150 mL) was treated portionwise at 0° C. with NBS (17.82 g, 100 mmol), then stirred for a further 2 h at 0° C. The mixture was concentrated under reduced pressure and the residue was dissolved in CH2Cl2. The solution was filtered through a short column of silica gel, and the product was recrystallised from MeOH to give tert-butyl 1-bromo-2-naphthylcarbamate (105) (24.09 g, 90%), as a white solid: mp 90-91° C.; 1H NMR [(CD3)2SO] δ 8.82 (s, 1H), 8.15 (d, J=8.5 Hz, 1H), 7.96 (d, J=9.6 Hz, 1H), 7.93 (d, J=9.3 Hz, 1H), 7.71 (d, J=8.8 Hz, 1H), 7.66 (t, J=7.7 Hz, 1H), 7.56 (t, J=7.4 Hz, 1H), 1.49 (s, 9H). Anal. (C15H16BrNO2) C, H, N, Br.

Workup

concentrationThe mixture was concentrated under reduced pressure
dissolutionthe residue was dissolved in CH2Cl2
filtrationThe solution was filtered through a short column of silica gel
customthe product was recrystallised from MeOH

Sources & evidence

ORD record: ord-f937262268cf4939aec177c48de232ca
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718688B2

Reaction notes

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