N,N,N',N'-Tetramethylethylenediamine → (4-Fluoro-5-isopropyl-2-methoxyphenyl)boronic acid

HRID 2283146Notes

Reaction equation

HRID 2283146 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[C:5]([F:11])=[CH:4][C:3]=1[O:12][CH3:13].C([Li])CCC.[B:19](OC(C)C)([O:24]C(C)C)[O:20]C(C)C.CN(CCN(C)C)C>C1(C)C=CC=CC=1>[F:11][C:5]1[C:6]([CH:8]([CH3:10])[CH3:9])=[CH:7][C:2]([B:19]([OH:24])[OH:20])=[C:3]([O:12][CH3:13])[CH:4]=1

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 21531Triisopropyl borateHCID 573894991-Bromo-4-fluoro-5-isopropyl-2-methoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 53363739(4-Fluoro-5-isopropyl-2-methoxyphenyl)boronic acidYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 2-bromo-4-isopropyl-5-fluoroanisole (88 wt % in toluene, 10.44 g, 37.2 mmol) in anhydrous toluene was cooled to −10° C. under N2 atmosphere, and 2.5 M, n-butyllithium solution in hexanes (16.36 ml, 40.69 mmol) was added slowly. After stirring at the same temperature for 10 minutes, the resulting solution was transferred to a cooled solution of triisopropyl borate (14.53 ml, 61.3 mmol) and TMEDA (2.80 ml, 18.59 mmol) in toluene slowly at −20° C. After stirring for 30 minutes, the reaction mixture was quenched with 3M H2SO4 (45 ml), and the resulting mixture was worked up as described in Step 4a to provide the title compound in 83% yield (6.62 g, 98.5 wt %).

Workup

  1. stirringAfter stirring for 30 minutes
  2. customthe reaction mixture was quenched with 3M H2SO4 (45 ml)

Sources & evidence

ORD record
ord-2ed12f450434435aa4a5c7be6c6b022b
Source dataset
uspto-grants-2015_09
Patent number
US09145348B2

Reaction notes

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