5-Bromo-benzo(b)thiophene-2-carboxylic acid → (5-Bromo-benzo[b]thiophen-2-yl)-methanol

HRID 1173821

반응식

HRID 1173821 반응식
[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[S:6][C:7]([C:9](O)=[O:10])=[CH:8][C:4]=2[CH:3]=1>C1COCC1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[S:6][C:7]([CH2:9][OH:10])=[CH:8][C:4]=2[CH:3]=1

참가 물질

3

반응물 1

HCID 7377375-Bromo-benzo(b)thiophene-2-carboxylic acid

생성물 1

HCID 21844218(5-Bromo-benzo[b]thiophen-2-yl)-methanol수율 51.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

Dissolve 5-bromo-benzo[b]thiophene-2-carboxylic acid (21.2 g, 82.5 mmol) in THF (150 mL). Cool to 0° C. with an ice bath. Add 2M BH3 dimethyl sulfide complex in THF (82.5 mL). Stir to room temperature over 2 hours. Quench by careful addition of water. Partition between ether and saturated NaHCO3, wash with water, brine, dry, and concentrate. Purify via column chromatography eluting with 3:1 hexanes:ethyl acetate to afford a white solid (10.3 g): 1H NMR (CDCl3) δ 7.87 (m, 1H), 7.67 (d, 1H), 7.41 (dd, 1H), 7.15 (m, 1H), 4.94 (d, 2H), 1.91 (t, 1H).

후처리

  1. customQuench by careful addition of water
  2. customPartition between ether and saturated NaHCO3
  3. washwash with water, brine
  4. customdry
  5. concentrationconcentrate
  6. customPurify via column chromatography
  7. washeluting with 3:1 hexanes

출처 및 근거

ORD 기록
ord-47624e7d3ee545ba976f65ea6d9ccd53
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834194B2

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