Hydrogen Bromide → 6-Bromo-1-tetralone

HRID 63612

반응식

HRID 63612 반응식
N([O-])=O.[Na+].N[C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10][CH2:9]2.[BrH:17]>O>[Br:17][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10][CH2:9]2

참가 물질

5

반응물 3

HCID 260Hydrogen Bromide2회HCID 3395376-Amino-1,2,3,4-tetrahydronaphthalen-1-oneHCID 23668193Sodium Nitrite

생성물 1

HCID 101050696-Bromo-1-tetralone수율 80%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of NaNO2 (2.35 g, 34 mmol) in water (10 mL) was added dropwise to the solution of 6-amino-1,2,3,4-tetrahydronaphthalen-1-one (5.0 g, 31 mmol) in 25% HBr (16 mL) at 0° C. The suspension was then transferred to a stirred mixture of CuBr (8.9 g, 62 mmol) in 48% HBr (30 mL) at 0° C. The resulting mixture was allowed to warm to rt and stirred for 1 h. The mixture was extracted with EtOAc, dried (Na2SO4), and concentrated. The residue was purified by silica gel chromatography (0%-60% EtOAc/Hex) to give 5.6 g (80%) of the title compound as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 2.10-2.16 (2H, m), 2.64 (2H, t, J=6.4 Hz), 2.94 (2H, t, J=6.0 Hz), 7.42 (1H, s), 7.44 (1H, s), 7.87 (1H, d, J=8.9 Hz). [M+H] calc'd for C10H9BrO, 225, 227. found 225, 227.

후처리

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (0%-60% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-60fe536885a24b3ebd69d37f8cb27bf5
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447046B2

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