Hexane → 2-(2-Bromoethyl)naphthalene

HRID 236413

반응식

HRID 236413 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:33]N1C(=O)CCC1=O.CCCCCC>C1C=CC=CC=1>[Br:33][CH2:12][CH2:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1

참가 물질

6

반응물 4

HCID 8058HexaneHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 738772-Naphthaleneethanol

생성물 1

HCID 2282702-(2-Bromoethyl)naphthalene

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

To a solution of 25 g (145 mmole) of 2-(2-naphthyl)ethanol and 67.9 g (259 mmole) of triphenylphosphine in 200 ml of benzene was added in portions 46.1 g (259 mmole) of N-bromosuccinimide. A temperature of 45°-50° was maintained by cooling the reaction mixture as needed in an ice bath. After the mixture was poured into 750 ml of hexane and filtered, the filtrate was diluted with an additional 400 ml of hexane and allowed to stand overnight. The solution was concentrated to dryness and the resultant solid was purified by chromatography on silica gel. The title compound (30.5 g), m.p. 55°-57°, was homogeneous by thin-layer chromatography (5%, 10%, and 15% by volume ethyl acetate-hexane on silica gel plates), and was used in subsequent reactions without further purification.

후처리

  1. temperatureA temperature of 45°-50° was maintained
  2. temperatureby cooling the reaction mixture
  3. customas needed in an ice bath
  4. filtrationfiltered
  5. additionthe filtrate was diluted with an additional 400 ml of hexane
  6. concentrationThe solution was concentrated to dryness
  7. customthe resultant solid was purified by chromatography on silica gel
  8. customwas used in subsequent reactions without further purification

출처 및 근거

ORD 기록
ord-46b89368cfbf462aace282a276fc3a70
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04644071

연결된 노트

불러오는 중…