Water → 4-Bromo-7-fluoro-1,2-dihydroisoquinolin-1-one

HRID 575562Notes

Reaction equation

HRID 575562 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][N:10](C)[C:11]2=[O:14])=[CH:6][CH:5]=1.O>C(O)(=O)C>[Br:1][C:8]1[C:7]2[C:12](=[CH:13][C:4]([F:3])=[CH:5][CH:6]=2)[C:11](=[O:14])[NH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 208001207-Fluoro-2-methylisoquinolin-1(2H)-one

Product 1

HCID 847030324-Bromo-7-fluoro-1,2-dihydroisoquinolin-1-oneYield 44%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
26 °C

Procedure

Bromine (3.8 g, 24 mmol) in acetic acid (6 mL) was added slowly to a mixture of 7-fluoro-2-methylisoquinolin-1-one (4 g, 22.4 mmol) in acetic acid (8 mL) at 0° C. After stirring at 26° C. for 2 h, the mixture was poured into water (100 mL) and the solid was collected by filtration. Purification by silica gel chromatography (PE:EA=20:1) gave the title compound (1.4 g, 44%) as an off-white solid. 1H NMR (CDCl3, 400 MHz) δ 8.11 (d, J=9.2 Hz, 1H), 7.84 (dd, J1=9.6 Hz, J2=4.8 Hz, 1H), 7.49-7.45 (m, 1H), 7.34 (s, 1H), 3.62 (3H, s). LCMS: 255.9 [M+H]+

Workup

  1. filtrationthe solid was collected by filtration
  2. customPurification by silica gel chromatography (PE:EA=20:1)

Sources & evidence

ORD record
ord-4817ac614cdc40c08c21ac25a573d068
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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