D-Phenylalanine → 3-(2-Bromophenyl)propionic acid

HRID 266035

반응식

HRID 266035 반응식
N([O-])=O.[Na+].N[C@@H:6]([C:14]([OH:16])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br-:17].[K+]>S(=O)(=O)(O)O>[CH:12]1[CH:13]=[C:8]([CH2:7][CH2:6][C:14]([OH:16])=[O:15])[C:9]([Br:17])=[CH:10][CH:11]=1

참가 물질

5

반응물 3

HCID 71567D-PhenylalanineHCID 253877Potassium BromideHCID 23668193Sodium Nitrite

생성물 1

HCID 3160103-(2-Bromophenyl)propionic acid수율 62%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

반응 조건

온도
0 °C

실험 절차

Sodium nitrite (10.3 g, 280 mmol) was added to a solution of D-phenylalanine (30.0 g, 181 mmol) and potassium bromide (73.5 g) in sulfuric acid (2.5N, 365 ml) over a period of one hour while maintaining the temperature of the reaction mixture at 0° C. The mixture was stirred for an additional hour at 0° C. and then for one hour at room temperature. The reaction solution was extracted with ether, the ether was back extracted with water, and the ether layer was dried over sodium sulfate. Ether was removed in vacuo, and distillation of the oily residue afforded 25.7 g of (R)-2-bromo-3-benzenepropanoic acid; b.p. 141° C. (0.55 mm of Hg); [α]D =+14.5° (c=2.4, chloroform).

후처리

  1. extractionThe reaction solution was extracted with ether
  2. extractionthe ether was back extracted with water
  3. dry with materialthe ether layer was dried over sodium sulfate
  4. customEther was removed in vacuo, and distillation of the oily residue

출처 및 근거

ORD 기록
ord-a9c7661f29dc43ce8ac5440c0f49aeec
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650408

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