1,2-Dibromoethane → 1,6-Dibromo-2-(2-bromoethoxy)naphthalene

HRID 734399

반응식

HRID 734399 반응식
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Br:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:13].[Br:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Br:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:13][CH2:16][CH2:15][Br:14]

참가 물질

5

반응물 3

HCID 78391,2-Dibromoethane2회HCID 11430Potassium CarbonateHCID 277682-Naphthol, 1,6-dibromo-

생성물 1

HCID 578454491,6-Dibromo-2-(2-bromoethoxy)naphthalene수율 69.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
0 °C

실험 절차

1,6-Dibromo-2-naphthol (15.0 g, 49.67 mmol) and 1,2-dibromoethane (46.7 g, 248.37 mmol) were added to a suspension of potassium carbonate (84.8 g, 74.51 mmol) in acetonitrile (500 mL) at rt. The reaction mixture was stirred for 48 h. Additional 1,2-dibromoethane (21.5 mL, 248.37 mmol) was added and the reaction mixture was stirred for 96 h at rt. The reaction mixture was cooled to 0° C. with an ice bath and filtered through a fritted glass funnel. The resulting filtrate was concentrated under reduced pressure to give the title compound (14.2 g, 69.9% yield) as a brown solid. GC/MS m/z 406 (M)+, RT 10.25 min; 1H NMR (400 MHz, acetone-d6) δ 14-8.09 (m, 2H), 7.96 (d, 1H), 7.71 (d, 1H), 7.54 (d, 1H), 4.64-4.60 (m, 2H), 3.90-3.86 (m, 2H).

후처리

  1. stirringthe reaction mixture was stirred for 96 h at rt
  2. filtrationfiltered through a fritted glass funnel
  3. concentrationThe resulting filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-26be35a68e7d47ae8aa3bb0fd838b34b
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592361B2

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