Sulfuric Acid → 3,4-Difluorophenylboric acid

HRID 486362

反応式

HRID 486362 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([F:9])[CH:3]=1.[Mg].[B:11]([O:20]C(C)C)([O:16]C(C)C)[O:12]C(C)C.S(=O)(=O)(O)O>O1CCCC1>[F:9][C:4]1[CH:3]=[C:2]([O:12][B:11]([OH:20])[OH:16])[CH:7]=[CH:6][C:5]=1[F:8]

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 21531Triisopropyl borateHCID 676754-Bromo-1,2-difluorobenzeneHCID 5462224Magnesium

生成物 1

HCID 218696723,4-Difluorophenylboric acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-65 °C

実験手順

A Grignard reagent solution prepared from 46.8 g of 1-bromo-3,4-difluorobenzene and 6 g of magnesium in 150 ml of tetrahydrofuran is added dropwise at -65° C. under nitrogen to a solution of 72.8 ml of triisopropyl borate in 200 ml of tetrahydrofuran. The mixture is stirred at -65° C. for 1 hour, warmed to 14°-20° C., treated dropwise with 100 ml of 10 percent (v/v) sulphuric acid, left to stand overnight and the separated salt is filtered off. The aqueous phase of the filtrate is separated and extracted with diethyl ether. The organic phases are combined, washed with sodium chloride solution, dried over sodium sulphate and evaporated. After boiling with hexane the residue gives 22.1 g of colourless 3,4-difluorophenylboric acid m.p. 275°-277.5° C. (sublimed).

後処理

  1. temperaturewarmed to 14°-20° C.
  2. waitleft
  3. waitto stand overnight
  4. filtrationthe separated salt is filtered off
  5. customThe aqueous phase of the filtrate is separated
  6. extractionextracted with diethyl ether
  7. washwashed with sodium chloride solution
  8. dry with materialdried over sodium sulphate
  9. customevaporated

出典と根拠

ORDレコード
ord-45bf03eb5ae64496aed4ad0a8ca2a381
出典データセット
uspto-grants-1994_03
特許番号
US05292452

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