Dichloromethane → Tert-butyl 3-bromo-2,2-dimethylpropanoic acid

HRID 1026555ノート

反応式

HRID 1026555 の反応式
C(N=C=NC(C)C)(C)C.[C:10](O)([CH3:13])([CH3:12])[CH3:11].ClCCl.[Br:18][CH2:19][C:20]([CH3:25])([CH3:24])[C:21]([OH:23])=[O:22]>[Cu]Cl.C(O)(=O)C>[C:10]([CH:19]([Br:18])[C:20]([CH3:25])([CH3:24])[C:21]([OH:23])=[O:22])([CH3:13])([CH3:12])[CH3:11]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 6386tert-ButanolHCID 12734DiisopropylcarbodiimideHCID 2719323-Bromo-2,2-dimethylpropanoic acid

生成物 1

HCID 86671389Tert-butyl 3-bromo-2,2-dimethylpropanoic acid

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 176Acetic Acid溶媒

実験手順

At room temperature under shielded light, to N,N′-diisopropylcarbodiimide (99.75 g) was added copper(I) chloride (1.57 g), and then tert-butanol (83 ml) was added dropwise over 20 minutes, followed by stirring for 4 days. The supernatant (78 ml) was added dropwise to a dichloromethane suspension (270 ml) of 3-bromo-2,2-dimethylpropanoic acid (49.4 g) at room temperature over 30 minutes, followed by stirring for 18 hours. Acetic acid (18.8 ml) was added, and stirred for 1 hour. The reaction suspension was filtered, and ice water and sodium hydrogen carbonate were added to the filtrate for neutralization. After the precipitate was filtered off, the organic layer separated from the filtrate was washed with saturated sodium hydrogen carbonate, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. After pentane was added to the residue, insolubles were filtered off, and the filtrate was concentrated under reduced pressure to afford tert-butyl 3-bromo-2,2-dimethylpropanoic acid (18.81 g).

後処理

  1. stirringby stirring for 18 hours
  2. stirringstirred for 1 hour
  3. filtrationThe reaction suspension was filtered
  4. additionice water and sodium hydrogen carbonate were added to the filtrate for neutralization
  5. filtrationAfter the precipitate was filtered off
  6. customthe organic layer separated from the filtrate
  7. washwas washed with saturated sodium hydrogen carbonate
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. additionAfter pentane was added to the residue, insolubles
  11. filtrationwere filtered off
  12. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-f1a6d1ee69184155bc34aff288c88b61
出典データセット
uspto-grants-2014_05
特許番号
US08729095B2

反応ノート

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