Water → 1-(3-Bromo-2-hydroxy-5-methylphenyl)ethan-1-one

HRID 45427

반응식

HRID 45427 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[Br:12]Br.O>ClCCl.[Fe]>[Br:12][C:7]1[C:2]([OH:1])=[C:3]([C:9](=[O:11])[CH3:10])[CH:4]=[C:5]([CH3:8])[CH:6]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 150682-Hydroxy-5-methylacetophenoneHCID 24408Bromine

생성물 1

HCID 111389181-(3-Bromo-2-hydroxy-5-methylphenyl)ethan-1-one수율 48%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 21.5 g (0.143 mol) of 28 in 40 mL of dry dichloromethane, 0.3 g of iron turnings was added. A solution of 10.7 mL (34.2 g, 0.215 mol) of bromine in 100 mL of dichloromethane was added dropwise with vigorous stirring for 20 min. This mixture was refluxed for 30 min, and then 300 mL of water was added. The organic layer was separated, and the aqueous layer was extracted with 2×100 mL of dichloromethane. The combined organic extracts were washed with saturated aqueous Na2SO3, dried over K2CO3, and then evaporated to dryness. Drying the residue in vacuum gave 15.7 g (48%) of 29 (bp 105-115° C./1 mm).

후처리

  1. temperatureThis mixture was refluxed for 30 min
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with 2×100 mL of dichloromethane
  4. washThe combined organic extracts were washed with saturated aqueous Na2SO3
  5. dry with materialdried over K2CO3
  6. customevaporated to dryness
  7. customDrying the residue in vacuum

출처 및 근거

ORD 기록
ord-9642d440da684f9394e48a7cdd79826a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541521B2

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