N-bromobutanimide → Ethyl 3-(2-bromophenyl)propanoate

HRID 724491

反応式

HRID 724491 の反応式
[O-]CC.[Na+].C(O)C.[CH2:8]([CH:15](C(C)=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Br:24]N1C(=O)CCC1=O>>[Br:24][C:14]1[C:9]([CH2:8][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:11]=[CH:12][CH:13]=1

参加物

4

反応物 3

HCID 67184N-bromobutanimideHCID 246929Ethyl alpha-benzylacetoacetateHCID 23706232Ethanol sodium ethoxide

生成物 1

HCID 10611137Ethyl 3-(2-bromophenyl)propanoate収率 83.7%

反応条件

温度
-35 °C

実験手順

To a 2 L 4-necked round bottom flask that was equipped with an overhead stirrer, an addition funnel, a condenser and a temperature-probe, was added the solution of sodium ethoxide/ethanol (21% wt. %, 161.8 g) at 20–25° C. under nitrogen. Ethyl 2-benzylacetoacetate (103.1 g, 0.454 mole) was added dropwise. The resulting solution was stirred at 20–25° C. for 30 minutes. The reaction mixture was then cooled to −35° C. with a dry ice/acetone bath. N-Bromosuccinimide (NBS; 97.95 g, 0.545 mole) was added portion-wise over 30 minutes. After the addition was over, the reaction mixture was stirred at −35° C. for 1 hr before warming up to 20–25° C. and it was stirred for an additional 2 hrs. The reaction was then quenched with water (400 mL) and ethyl acetate (600 mL) was added. The layers were separated and the product was extracted from aqueous layer with ethyl acetate (400 mL×3). The combined organic layers was washed with saturated sodium bicarbonate twice (400 mL×2), water twice (400 mL×2) and brine (500 mL). After the removal of solvent, the product (crude, 132 g) was distilled under reduced pressure. Ethyl 2-bromo-3-benzenepropanoate (97.7 g) was obtained at yield 83.7%.

後処理

  1. customTo a 2 L 4-necked round bottom flask that was equipped with an overhead stirrer, an addition funnel, a condenser
  2. additionAfter the addition
  3. stirringwas stirred at −35° C. for 1 hr
  4. temperaturebefore warming up to 20–25° C.
  5. stirringit was stirred for an additional 2 hrs
  6. customThe reaction was then quenched with water (400 mL) and ethyl acetate (600 mL)
  7. additionwas added
  8. customThe layers were separated
  9. extractionthe product was extracted from aqueous layer with ethyl acetate (400 mL×3)
  10. washThe combined organic layers was washed with saturated sodium bicarbonate twice (400 mL×2), water twice (400 mL×2) and brine (500 mL)
  11. customAfter the removal of solvent
  12. distillationthe product (crude, 132 g) was distilled under reduced pressure

出典と根拠

ORDレコード
ord-6ee81d631b6f485f8bf85c40c0491d24
出典データセット
uspto-grants-2006_11
特許番号
US07141694B2

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