Hydrochloric Acid → 3-Bromo-4-fluorobenzyl Alcohol

HRID 851635

反応式

HRID 851635 の反応式
[BH4-].[Na+].[Cl-].[Al+3].[Cl-].[Cl-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([Br:17])[CH:11]=1.Cl>COCCOCCOC>[F:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][OH:8])=[CH:11][C:12]=1[Br:17]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 6451240Aluminum(III) ChlorideHCID 7018022Methyl 3-bromo-4-fluorobenzoate

生成物 1

HCID 27733513-Bromo-4-fluorobenzyl Alcohol収率 91.2%

試薬・触媒・溶媒 1

HCID 8150Diglyme溶媒

実験手順

First 3.8 g (0.1 mole) of sodium borohydride and then 4.5 g (0.033 mole) of aluminum chloride were added in portions to a solution of 23.3 g (0.1 mole) of 4-fluoro-3-bromobenzoic acid methyl ester in 50 ml of diglyme at 5° C. The mixture was subsequently stirred, without cooling, until the exothermic reaction had ended (a rise in temperature up to about 50° C.) and the reaction was then allowed to go to completion in the course of 1 hour at 100° C. The reaction solution was then poured onto a mixture of 125 ml of icewater and 12 ml of concentrated hydrochloric acid and the benzyl alcohol which had separated out was separated off and distilled in vacuo. 18.7 g (91% of theory) of 4-fluoro-3-bromobenzyl alcohol were obtained in this manner as a colorless oil with a boiling point of 65° to 70° C. (0.1 mbar). "One-pot process"

後処理

  1. temperaturewithout cooling, until the exothermic reaction
  2. customup to about 50° C.
  3. customto go to completion in the course of 1 hour at 100° C
  4. customthe benzyl alcohol which had separated out
  5. customwas separated off
  6. distillationdistilled in vacuo

出典と根拠

ORDレコード
ord-19c336527596475ca3271093f5cf9fda
出典データセット
uspto-grants-1983_05
特許番号
US04386035

関連ノート

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