Triethylamine → 2-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

HRID 2098746Notes

Reaction equation

Br[C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(N(CC)CC)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[BH3:42].[OH:43][C:44]([C:47]([OH:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45]>O1CCOCC1.C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:9][C:3]1[C:2]([B:42]2[O:50][C:47]([CH3:49])([CH3:48])[C:44]([CH3:46])([CH3:45])[O:43]2)=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-bromo-2-methylaniline (1.00 g) in dioxane (15 mL) was added triethylamine (3.0 mL), Pd(OAc)2 (60 mg), 2-dicyclohexylphosphinobiphenyl (377 mg) and pinacol borane (2.34 mL) and the reaction mixture was heated to 80° C. for 1 hour. The reaction mixture was then cooled, diluted with ethyl acetate, and reduced in vacuo. The residue was purified using flash chromatography to yield 2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (1.07 g).

Workup

temperatureThe reaction mixture was then cooled
customThe residue was purified

Sources & evidence

ORD record: ord-e224139111b444839fb3cede7a08ee75
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450315B2

Reaction notes

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