2-Bromopropane → Benzenamine, 4-chloro-2-fluoro-5-(1-methylethoxy)-

HRID 263381

Reaction equation

[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.Br[CH:12]([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>>[Cl:9][C:5]1[C:6]([O:8][CH:12]([CH3:14])[CH3:13])=[CH:7][C:2]([NH2:1])=[C:3]([F:10])[CH:4]=1

Participants

Reactant 3

HCID 63582-Bromopropane

HCID 11430Potassium Carbonate

HCID 1586545-Amino-2-chloro-4-fluorophenol

Product 1

HCID 158649Benzenamine, 4-chloro-2-fluoro-5-(1-methylethoxy)-Yield 62%

Procedure

A stirring mixture of 5-amino-2-chloro-4-fluorophenol (22.0 g, 136.19 mmol), 2-bromopropane (38.4 mL, 50.25 g, 408.57 mmol) and potassium carbonate (37.6 g, 273.0 mmol) was heated at reflux for 17 h. The reaction mixture was cooled and filtered. The filtrate was evaporated to dryness under reduced pressure. Flash chromatography yielded the title compound of Step A as a brown oil (17.2 g). 1H NMR (CDCl3): δ7.02 (d, 1H), 6.44 (d, 1H) 4.38 (q, 1H), 3.81 (br s,2H), 1.33 (d,6H). IR (cm-1): 3378.4, 3475.6.

Workup

temperaturewas heated
temperatureat reflux for 17 h
temperatureThe reaction mixture was cooled
filtrationfiltered
customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record: ord-e7557914f99c40acbe835f6180c02ff1
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05643855

Linked notes

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