Water → 3-(4-Bromophenoxy)-6-methoxybenzo[b]thiophene

HRID 332855노트

반응식

HRID 332855 반응식
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:8]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:9]=3[S:10](=O)(=O)[CH:11]=2)=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:8]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:9]=3[S:10][CH:11]=2)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 14487Diisobutylaluminum hydrideHCID 9855836Potassium sodium tartarateHCID 867306373-(4-Bromophenoxy)-6-methoxybenzo[b]thiophene 1,1-dioxide

생성물 1

HCID 867306383-(4-Bromophenoxy)-6-methoxybenzo[b]thiophene수율 84.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매2회

반응 조건

온도
75 °C

실험 절차

To a solution of 3-(4-bromophenoxy)-6-methoxybenzo[b]thiophene 1,1-dioxide (2.47 g, 6.73 mmol) in THF (90 mL) was added DIBAL-H (1.0 M in DCM, 33.6 mL, 33.6 mmol) in one portion. The mixture was heated to 75° C. for 2 h after which time the reaction was cooled to room temperature and quenched with EtOAc (32.9 mL, 336 mmol). The resulting solution was stirred for 10 min before carefully adding 75 mL of water and potassium sodium tartrate (33.100 g, 117 mmol). The mixture was vigorously stirred for 10 min and diluted with 75 mL EtOAc. The organic layer was collected, dried with anhydrous MgSO4 and concentrated in vacuo to afford 3-(4-bromophenoxy)-6-methoxybenzo[b]thiophene (1.9 g, 5.67 mmol, 84% yield) as a white solid which was used without further purification. 1H NMR (400 MHz, CDCl3) δ ppm=3.81 (s, 3H), 6.46 (s, 1H), 6.90 (d, J=9.09 Hz, 3H), 7.16-7.22 (m, 1H), 7.31-7.40 (m, 2H), 7.46 (d, J=9.09 Hz, 1H). LC/MS (m/z, MH+): 336.8.

후처리

  1. temperaturewas cooled to room temperature
  2. stirringThe mixture was vigorously stirred for 10 min
  3. customThe organic layer was collected
  4. dry with materialdried with anhydrous MgSO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8c656a78eb674fa19c4249b658756066
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877801B2

반응 노트

불러오는 중…