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

HRID 1642841ノート

反応式

HRID 1642841 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-e14c8e68c695457686e0ff4e8e86daf4
出典データセット
uspto-grants-2012_02
特許番号
US08119663B2

反応ノート

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