Hydrochloric Acid → [4-Methyl-3-(trifluoromethyl)phenyl]boronic acid

HRID 1642841Notes

Reaction equation

HRID 1642841 reaction equation
C([Li])CCC.[CH3:6][C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][C:8]=1[C:14]([F:17])([F:16])[F:15].C[O:19][B:20](C)[O:21]C.Cl>CCCCCC.C1COCC1>[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([B:20]([OH:21])[OH:19])=[CH:9][C:8]=1[C:14]([F:17])([F:16])[F:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 138991Boronic acid, methyl-, dimethyl esterHCID 27756354-Methyl-3-(trifluoromethyl)bromobenzeneHCID 178418339Butyllithium

Product 1

HCID 45158669[4-Methyl-3-(trifluoromethyl)phenyl]boronic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

At −78° C., 9.2 ml (1.5 g, 23.0 mmol) of a 2.5M solution of n-butyllithium in hexane were initially charged in 30 ml of THF. 5.0 g (20.9 mmol) of 4-methyl-3-(trifluoromethyl)bromobenzene were dissolved in 15 ml of THF and slowly added dropwise. 3.3 g (31.4 mmol) of trimethylboronic acid were then added dropwise. The mixture was stirred at −78° C. for 2 h, and 11 ml of 2 N hydrochloric acid were then added. The mixture was allowed to warm to RT, and the organic phase was separated off. The solvent was removed under reduced pressure and the residue was recrystallized from n-heptane. Yield: 2.6 g (60% of theory)

Workup

  1. additionslowly added dropwise
  2. temperatureto warm to RT
  3. customthe organic phase was separated off
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was recrystallized from n-heptane

Sources & evidence

ORD record
ord-e14c8e68c695457686e0ff4e8e86daf4
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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