Sodium borohydride → 3-(4-Bromophenoxy)-6-methoxybenzo[b]thiophene 1,1-dioxide

HRID 632682ノート

反応式

HRID 632682 の反応式
Br[C:2]1[S:6](=[O:8])(=[O:7])[C:5]2[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:4]=2[C:3]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=1.[BH4-].[Na+]>CO.CS(C)=O>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:3]2[C:4]3[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:5]=3[S:6](=[O:8])(=[O:7])[CH:2]=2)=[CH:17][CH:18]=1

参加物

5

反応物 2

HCID 4311764Sodium borohydride2 回HCID 867306362-Bromo-3-(4-bromophenoxy)-6-methoxybenzo[b]thiophene 1,1-dioxide

生成物 1

HCID 867306373-(4-Bromophenoxy)-6-methoxybenzo[b]thiophene 1,1-dioxide

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 887Methanol溶媒

反応条件

温度
10 °C

実験手順

To a solution of 2-bromo-3-(4-bromophenoxy)-6-methoxy-benzo[b]thiophene 1,1-dioxide (180 g, 403 mmol) in MeOH (150 mL) and DMSO (1300 mL) at 0° C. (internal temperature was at 5° C.) was added the first portion of NaBH4 (15 g, 396.5 mmol). Internal temperature rose quickly to 40° C. and H2 gas release was observed. The mixture was stirred in an ice bath for 30 min (internal temperature cooled down to 10° C.). The second portion of NaBH4 (15.5 g, 409.7 mmol) was added. The resulting mixture was stirred for 30 minutes after which time the reaction was quenched with water (2000 mL) over 1 hour. The resulting precipitate was collected, air dried over 18 hours, then washed with heptane to afford 3-(4-bromophenoxy)-6-methoxybenzo[b]thiophene 1,1-dioxide as an off white solid which was used without further purification. 1H NMR (400 MHz, CDCl3) δ ppm=3.85 (s, 3 H), 5.38 (s, 1 H), 7.02-7.08 (m, 3 H), 7.22 (d, J=2.53 Hz, 1 H), 7.47-7.60 (m, 3 H).

後処理

  1. customrose quickly to 40° C.
  2. stirringThe resulting mixture was stirred for 30 minutes after which time the reaction
  3. customwas quenched with water (2000 mL) over 1 hour
  4. customThe resulting precipitate was collected
  5. customair dried over 18 hours
  6. washwashed with heptane

出典と根拠

ORDレコード
ord-3463e38a353347089d1bb6dbd25f6054
出典データセット
uspto-grants-2016_04
特許番号
US09321746B2

反応ノート

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