Boron tribromide → 2-methyl-1H-indol-5-ol

HRID 129380

반응식

HRID 129380 반응식
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[CH:6]2.B(Br)(Br)Br.O.C(Cl)(Cl)Cl>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[CH:6]2

참가 물질

5

반응물 3

HCID 25134Boron tribromideHCID 706425-Methoxy-2-methylindoleHCID 22418719Chloroform water

생성물 1

HCID 833362-methyl-1H-indol-5-ol수율 67.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a -65° C. solution of 8.6 g (53.4 m mol) 5-methoxy-2-methyl indole in 110 mL of CH2Cl2 was added dropwise 30.4 g (117 m mol) of boron tribromide. The reaction was allowed to warm to room temperature and stirred for 30 minutes. After cooling the mixture to 5° C., 200 mL of 50% water/chloroform was cautiously added. The aqueous layer was separated and the pH adjusted to 5.8 with aqueous sodium hydroxide. Extracting the mixture twice with 100 mL of ethyl acetate, followed by drying (Na2SO4), filtering and concentrating provided 5.3 g of the product as a yellow solid, mp 124°-126° C. 1H NMR (60 MHz, 20% DMSO d6 /CDCl3) δ 8.05 (s, 1H, NH), 7.05 (d, J=8 Hz, 1H), 6.80 (d, J=2 Hz, 1H), 6.55 (dd, J=2, 8 Hz, 1H), 5.90 (broad s, 1H, indole CH), 2.40 (s, 3H).

후처리

  1. temperatureAfter cooling the mixture to 5° C.
  2. customThe aqueous layer was separated
  3. extractionExtracting the mixture twice with 100 mL of ethyl acetate
  4. dry with materialby drying (Na2SO4)
  5. filtrationfiltering
  6. concentrationconcentrating

출처 및 근거

ORD 기록
ord-9712532fcbc34ab18b8806c8f119b740
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05468641

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