1-Bromohexane → 2-Bromo-6-(hexyloxy)naphthalene

HRID 129786

반응식

HRID 129786 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:8]=2)[CH:3]=1

참가 물질

5

반응물 3

HCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 271446-Bromo-2-naphthalenol

생성물 1

HCID 45355832-Bromo-6-(hexyloxy)naphthalene수율 81%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a stirred solution of 4.46 g (20.0 mmol) of 6-bromo-2-naphthalenol (obtained from Aldrich Chemical Company (#B7,340-6) and used without purification), in 20 mL of DMF at room temperature under argon was added 480 mg (20 mmol) of 95% sodium hydride over the course of 15 min. The resulting light yellow solution was stirred 30 min and 3.5 mL (22 mmol) of 1-bromohexane was added. The reaction was heated to 50° C. and stirred for 60 min. The reaction was quenched with ice water, the resultings solids filtered, washed with water and dried in vacuo at 60° C. Purification of the residue by chromatography on silica gel (5×20 cm column, hexanes as elutant) gave 5.00 g, 81% yield, of title compound as a colorless oil.

후처리

  1. stirringstirred for 60 min
  2. customThe reaction was quenched with ice water
  3. filtrationthe resultings solids filtered
  4. washwashed with water
  5. customdried in vacuo at 60° C
  6. customPurification of the residue by chromatography on silica gel (5×20 cm column, hexanes as elutant)
  7. customgave 5.00 g, 81% yield

출처 및 근거

ORD 기록
ord-ea0be3f4da6145b1a42c817acc44334a
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05470845

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