Di-tert-butyl dicarbonate → HCID 86675119, compound

HRID 587661Notes

Reaction equation

Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([Cl:15])[CH:3]=1.Br[C:17]1C=CC(C(O)=O)=C(Cl)[CH:18]=1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>C1COCC1.CN(C1C=CN=CC=1)C.CCOC(C)=O>[Cl:15][C:4]1[CH:3]=[C:2]([CH:17]=[CH2:18])[CH:14]=[CH:13][C:5]=1[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

Conditions

Temperature: 25 °C

Procedure

tert-Butyl 4-bromo-2-chlorobenzoate (AI18) To a stirred solution of 4-bromo-2-chlorobenzoic acid (5 g, 21.37 mmol) in THF (30 mL) was added di-tert-butyl dicarbonate (25.5 g, 25.58 mmol), TEA (3.2 g, 31.98 mmol) and DMAP (0.78 g, 6.398 mmol), and the reaction mixture was stirred at 25° C. for 18 h. The reaction mixture was diluted with EtOAc and washed with water. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 100-200 mesh; eluting with 2-3% EtOAc in n-hexane) to afford the title compound as a liquid (3.2 g, 51%): 1H NMR (400 MHz, CDCl3) δ 7.62 (m, 2H), 7.44 (d, J=8.4 Hz, 1H), 1.59 (s, 9H); ESIMS m/z 290.10 ([M+H]+); IR(thin film) 1728 cm−1.

Workup

washwashed with water
washThe combined organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography (SiO2, 100-200 mesh; eluting with 2-3% EtOAc in n-hexane)

Sources & evidence

ORD record: ord-c24bc208a4c04541b225ff1c04e740d2
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226501B2

Reaction notes

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