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

HRID 129380

反応式

HRID 129380 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 833362-methyl-1H-indol-5-ol収率 67.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9712532fcbc34ab18b8806c8f119b740
出典データセット
uspto-grants-1995_11
特許番号
US05468641

関連ノート

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