Trimethyl borate → 3,5-Difluoro-2-methylsulfanylphenylboronic acid

HRID 1513934ノート

反応式

HRID 1513934 の反応式
C([Mg]Cl)(C)C.Br[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([F:14])[C:8]=1[S:15][CH3:16].C[O:18][B:19](OC)[O:20]C>O1CCCC1>[F:14][C:9]1[C:8]([S:15][CH3:16])=[C:7]([B:19]([OH:20])[OH:18])[CH:12]=[C:11]([F:13])[CH:10]=1

参加物

5

反応物 3

HCID 8470Trimethyl borateHCID 670051631-Bromo-3,5-difluoro-2-methylsulfanylbenzeneHCID 178418918HCID 178418918、化合物

生成物 1

HCID 575525453,5-Difluoro-2-methylsulfanylphenylboronic acid収率 61.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
40 °C

実験手順

Charge a flask with isopropyl magnesium chloride (145 mL, 2M in THF, 290 mmol) and dilute with tetrahydrofuran (150 mL) and heat to 40° C. under nitrogen. Add 1-bromo-3,5-difluoro-2-methylsulfanyl-benzene (28 g, 117 mmol) slowly over 5 minutes. After 30 minutes, cool the reaction to 0° C. and add trimethylborate (46 mL, 410 mmol) diluted with tetrahydrofuran (100 mL) via an addition funnel over 5 minutes. Partition the resulting gelatinous mixture between methylene chloride and 1N HCl. Acidify the aqueous layer to pH˜1 (if needed) and vigorously stir the biphasic mixture until all solids are dissolved. Separate the organic layer. Dry over sodium sulfate, filter and concentrate. Triturate with hexanes and filter to yield 14.7 g (61%) of the title compound.

後処理

  1. temperaturecool
  2. customthe reaction to 0° C.
  3. customPartition the resulting gelatinous mixture between methylene chloride and 1N HCl
  4. dissolutionare dissolved
  5. customSeparate the organic layer
  6. dry with materialDry over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate
  9. customTriturate with hexanes
  10. filtrationfilter

出典と根拠

ORDレコード
ord-5b5f1cd02b7f40bcac7180954cd8d843
出典データセット
uspto-grants-2012_07
特許番号
US08217032B2

反応ノート

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