Water → 1-(bromoacetyl)-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole

HRID 1014312Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (33.6 g, 173 mmol) in CH.2Cl2 (150 mL) was added dropwise to a mixture of bromoacetylchloride (54.5 g, 346 mmol) and K2CO3 (53.0 g, 381 mmol) in CH2Cl2 (150 mL). The resulting solution was stirred at 0° C. for 1 hour, then warmed up RT for 4 hours. Water (150 mL) was added and the mixture was extracted with CH2Cl2 (2×100 mL). The organic phase was dried over Na2SO4, the solvent was removed to yield the 1-(bromoacetyl)-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (54.2 g, 99%). 1HNMR (400 MHz, DMSO) δ ppm 2.47(s, 2H), 3.25 (m, 2 H), 3.87 (s, 3 H), 4.21 (m, 2 H), 7.34 (s, 1 H), 8.42 (s, 1 H).

Workup

temperaturewarmed up RT for 4 hours
extractionthe mixture was extracted with CH2Cl2 (2×100 mL)
dry with materialThe organic phase was dried over Na2SO4
customthe solvent was removed

Sources & evidence

ORD record: ord-93c69cd3de034f3499b8dd206538a522
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981903B2

Reaction notes

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