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

HRID 332855ノート

反応式

HRID 332855 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
75 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8c656a78eb674fa19c4249b658756066
出典データセット
uspto-grants-2014_11
特許番号
US08877801B2

反応ノート

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