Trifluoroacetic acid → 1-Benzyl-4-bromo-2,5-dimethoxybenzene

HRID 1486832

반응식

HRID 1486832 반응식
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=O)=[C:4]([O:18][CH3:19])[CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.[NH4+].[Cl-]>C(Cl)Cl.O>[CH2:10]([C:5]1[CH:6]=[C:7]([O:8][CH3:9])[C:2]([Br:1])=[CH:3][C:4]=1[O:18][CH3:19])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 25517Ammonium ChlorideHCID 67466544(4-Bromo-2,5-dimethoxyphenyl)(phenyl)methanone

생성물 1

HCID 900142701-Benzyl-4-bromo-2,5-dimethoxybenzene수율 98%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of (4-bromo-2,5-dimethoxyphenyl)(phenyl)methanone (100 mg, 0.311 mmol) in 0.2 mL of anhydrous DCM (C=1.5M), were successively added dropwise trifluoroacetic acid (0.24 mL, 10 eq) and triethylsilane (0.2 mL, 4 eq). After 16 h of stirring at r.t., the reaction mixture was hydrolyzed with a saturated NH4Cl solution (5 mL). The layers were diluted with 20 mL of DCM and 20 mL of water and then separated. The aqueous layer was extracted twice with DCM (2×10 mL) The combined organic phase was washed twice with a saturated NaHCO3 solution (2×20 mL), brine (2×20 mL), dried over MgSO4, filtered and concentrated in vacuo. The product was obtained pure enough for further reaction in 98% yield (93.4 mg). 1H NMR (300 MHz, CDCl3) δ 7.34-7.25 (m, 2H), 7.24-7.17 (m, 3H), 7.08 (s, 1H), 6.69 (s, 1H), 3.95 (s, 2H), 3.78 (s, 3H), 3.78 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 151.9 (C), 150.1 (C), 140.4 (C), 129.9 (C), 128.9 (CH), 128.5 (CH), 126.1 (CH), 116.1 (CH), 115.0 (CH), 109.1 (C), 57.0 (OCH3), 56.3 (OCH3), 35.9 (CH2Bn); MS (ESI) m/z: 324.5, 326.1 [M+NH4, 79Br, 81Br]+; 630.3, 632.0, 634.2 [2M+NH4, 79Br, 81Br]+.

후처리

  1. customseparated
  2. extractionThe aqueous layer was extracted twice with DCM (2×10 mL) The combined organic phase
  3. washwas washed twice with a saturated NaHCO3 solution (2×20 mL), brine (2×20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was obtained pure enough for further reaction in 98% yield (93.4 mg)

출처 및 근거

ORD 기록
ord-88ac974de66b4622ad2bda627e7d8eaf
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428500B2

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