Water → HCID 86707275, compound

HRID 576067Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].O.B1(C=C)OB([CH:14]=[CH2:15])OB(C=C)O1.C1C=CN=CC=1.Br[C:27]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:28]=1[NH2:29]>COCCOC.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:14]([C:27]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:28]=1[NH2:29])=[CH2:15]

Participants

Conditions

Temperature: 105 °C

Procedure

Tetrakis(triphenylphosphine)palladium (289 mg, 0.250 mmol), potassium carbonate (829 mg, 6.00 mmol), water (4 mL) and 2,4,6-trivinylcyclotriboroxane-pyridine complex (722 mg, 3.00 mmol) were successively added to a solution of 2-bromo-4-fluoroaniline (950 mg, 5.00 mmol) in 1,2-dimethoxyethane (10 mL) under an argon atmosphere. The mixture was heated to an external temperature of 105° C. and stirred for 7 hr. The mixture was diluted with ethyl acetate, washed with brine and dried over anhydrous sodium sulfate. Thereafter, the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→2:1) to afford 2-ethenyl-4-fluoroaniline as a reddish brown oil (458 mg).

Workup

washwashed with brine
dry with materialdried over anhydrous sodium sulfate
filtrationThereafter, the desiccant was filtered off
concentrationfollowed by concentration under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→2:1)

Sources & evidence

ORD record: ord-d7d54d4a129d41b58f950a52fbdc6242
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09035059B2

Reaction notes

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