Hydrochloric Acid → 4-(2-(Pyridin-4-yl)ethynyl)phenol

HRID 33928

반응식

HRID 33928 반응식
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1.[OH-].[Na+].Cl>ClCCl>[N:18]1[CH:19]=[CH:20][C:15]([C:14]#[C:13][C:10]2[CH:9]=[CH:8][C:7]([OH:6])=[CH:12][CH:11]=2)=[CH:16][CH:17]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 45952534-[2-(4-Methoxyphenyl)ethynyl]pyridine

생성물 1

HCID 597974994-(2-(Pyridin-4-yl)ethynyl)phenol

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Boron tribromide (1M in dichloromethane, 9.7 mL, 9.7 mmol) was added at 0° C. to a solution of 4-(2-(4-methoxyphenyl)ethynyl)pyridine (810 mg, 3.88 mmol) in dichloromethane (10 mL) and the mixture was stirred at RT for 5 h. Aqueous 1 N sodium hydroxide (20 mL) was added and after 40 min the pH was brought between 7 and 8 by addition of 1 N HCl. The resulting mixture was extracted with 4:1 dichloromethane:2-propanol (3×30 mL). The organic layers were dried, concentrated and evaporated and the residue chromatographed on silica in a gradient from 25% to 80% ethyl acetate-hexanes giving a brown solid. Yield 450 mg, 60%. 1H NMR (CDCl3 containing CD3OD, 400 mHz) δ 8.50 (br, 2H), 7.38 (br, 2H), 7.37 (d, 2H, J=8.7 Hz), 6.77 (d, 2H, J=8.7 Hz), 3.11 (br, 2H, OH+H2O). MS (AP+) m/e 196 (MH+).

후처리

  1. extractionThe resulting mixture was extracted with 4:1 dichloromethane
  2. customThe organic layers were dried
  3. concentrationconcentrated
  4. customevaporated
  5. customthe residue chromatographed on silica in a gradient from 25% to 80% ethyl acetate-hexanes giving a brown solid

출처 및 근거

ORD 기록
ord-be71155294ec46b4b9fc6bd51b289847
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429665B2

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