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

HRID 1642841노트

반응식

HRID 1642841 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-e14c8e68c695457686e0ff4e8e86daf4
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119663B2

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