Hydrochloric Acid → 2-(2-Chloro-3-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

HRID 1049116노트

반응식

HRID 1049116 반응식
[Cl:1][C:2]1[C:7]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]2)=[CH:6][CH:5]=[CH:4][C:3]=1[OH:17].[C:18](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O.Cl>CN(C=O)C>[Cl:1][C:2]1[C:3]([O:17][CH3:18])=[CH:4][CH:5]=[CH:6][C:7]=1[B:8]1[O:12][C:11]([CH3:13])([CH3:14])[C:10]([CH3:16])([CH3:15])[O:9]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 573742422-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

생성물 1

HCID 450369072-(2-Chloro-3-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane수율 85.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 2-chloro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (830 g, 3.26 mol) in dry DMF (4.15 L) was added potassium carbonate (1126.4 g, 8.15 mol) under an inert atmosphere. Me2SO4 (402 mL, 4.24 mol) was added slowly to control the resulting exotherm (addition over 30 minutes gave a temperature rise from 28° C. to 55° C.) and after complete addition the reaction was stirred for 10 minutes. The reaction mixture was added to stirring HCl (5.98 L, 2 N, aq.) very slowly to control effervescence and the resulting precipitate stirred for 2 hours. The solids were filtered and washed with water (1 L) and dried in a vacuum oven over drying agent for 4 days to give 2-(2-chloro-3-methoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 7a as a white powder (746.7 g, 2.78 mol, 85%).

후처리

  1. additionaddition over 30 minutes
  2. customgave a temperature rise from 28° C. to 55° C.) and
  3. additionafter complete addition the reaction
  4. additionThe reaction mixture was added
  5. stirringthe resulting precipitate stirred for 2 hours
  6. filtrationThe solids were filtered
  7. washwashed with water (1 L)
  8. customdried in a vacuum oven
  9. customover drying agent for 4 days

출처 및 근거

ORD 기록
ord-91339e3c4fd342439589461a5c05b105
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382214B2

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