Sodium borohydride → 1-Bromo-3-fluorobenzyl alcohol

HRID 1670596ノート

反応式

HRID 1670596 の反応式
[Br:1][C:2]1([CH:9]=[CH:8][CH:7]=[C:6]([F:10])[CH2:5]1)[CH:3]=[O:4].[BH4-].[Na+]>CO.C(OCC)(=O)C>[Br:1][C:2]1([CH:9]=[CH:8][CH:7]=[C:6]([F:10])[CH2:5]1)[CH2:3][OH:4]

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 866319341-Bromo-3-fluorobenzaldehyde

生成物 1

HCID 673357701-Bromo-3-fluorobenzyl alcohol収率 100%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To 1-bromo-3-fluorobenzaldehyde (1.60 kg, 7.91 mol) in methanol (14 L) at 0° C. add sodium borohydride (284 g, 7.93 mol) in portions over 30 min to control the exotherm and gas evolution. After 15 min, quench with water (500 mL) and concentrate to obtain a yellow oil. Dissolve the oil in ethyl acetate (6 L) and wash with water (3 L). Extract the aqueous layer with ethyl acetate (1 L). Wash the combined organic phases with brine (2 L), dry over sodium sulfate, filter, and concentrate to obtain the title compound as an orange oil (1614 g, 100%). 1H NMR (CDCl3) δ 7.40 (d, 1H), 7.18 (m, 1H), 7.07 (t, 1H), 4.86 (s, 2H).

後処理

  1. customquench with water (500 mL)
  2. concentrationconcentrate
  3. customto obtain a yellow oil
  4. washwash with water (3 L)
  5. extractionExtract the aqueous layer with ethyl acetate (1 L)
  6. washWash the combined organic phases with brine (2 L)
  7. dry with materialdry over sodium sulfate
  8. filtrationfilter
  9. concentrationconcentrate

出典と根拠

ORDレコード
ord-5d0c13cdd0a249bb8b46752edce60c5b
出典データセット
uspto-grants-2011_08
特許番号
US07994164B2

反応ノート

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