1-(3-Bromopropoxy)-4-chlorobenzene → 3-(4-Chlorophenoxy)propyl acetohydroxamate

HRID 2121072노트

반응식

HRID 2121072 반응식
O.[C:2]([NH:5][O-:6])(=[O:4])[CH3:3].[K+].[Cl:8][C:9]1[CH:19]=[CH:18][C:12]([O:13][CH2:14][CH2:15][CH2:16]Br)=[CH:11][CH:10]=1.[K+].[Br-]>COCCO>[C:2]([NH:5][O:6][CH2:16][CH2:15][CH2:14][O:13][C:12]1[CH:11]=[CH:10][C:9]([Cl:8])=[CH:19][CH:18]=1)(=[O:4])[CH3:3]

참가 물질

5

반응물 3

HCID 2235341-(3-Bromopropoxy)-4-chlorobenzeneHCID 253877Potassium BromideHCID 23700527Potassium acetohydroxamate hydrate

생성물 1

HCID 109776663-(4-Chlorophenoxy)propyl acetohydroxamate수율 105.8%

시약·촉매·용매 1

HCID 80192-Methoxyethanol용매2회

반응 조건

온도
50 °C

실험 절차

To a solution of 0.91 kg (8.0 moles) of potassium acetohydroxamate hydrate in 4.96 kg of 2-methoxyethanol solution was added 1650 g (6.62 moles) of 3-(4-chlorophenoxy) propyl bromide. An additional 200 mL of 2-methoxyethanol was added and the reaction mixture was heated 2 hours at 50° C. After cooling to room temperature the KBr was removed by filtration and washed with 100 mL of 2-methoxyethanol. The filtrate and washings were concentrated on a rotovap, diluted with 1.0 L of EtOAc, and washed with a 600 mL and a 400 mL portion of water before concentration at high vacuum to yield 1707 g of crude 3-(4-chlorophenoxy)propyl acetohydroxamate which was used without further purification. This crude material was dissolved in 5.0 L of methanol and 640 g of conc. HCL was added. After 15 hr the starting material was consumed, as determined by TLC utilizing the diazonium spray. The mixture was concentrated at oil pump vacuum to give 1537 g of crude product which was used without further purification. A sample recrystallized from EtOAc melted 115-116° C.

후처리

  1. customwas removed by filtration
  2. washwashed with 100 mL of 2-methoxyethanol
  3. concentrationThe filtrate and washings were concentrated on a rotovap
  4. additiondiluted with 1.0 L of EtOAc
  5. washwashed with a 600 mL
  6. concentrationa 400 mL portion of water before concentration at high vacuum

출처 및 근거

ORD 기록
ord-f0b651fe0ec14f8f9a3b362ff516de68
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06693217B2

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