Water → tert-butyl (2E)-3-[2-(bromomethyl)-4-methylphenyl]acrylate

HRID 64422노트

반응식

HRID 64422 반응식
O[CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1/[CH:10]=[CH:11]/[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(Br)(Br)(Br)[Br:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1.C(OCC)(=O)C>[Br:20][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1/[CH:10]=[CH:11]/[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

참가 물질

7

반응물 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86713430tert-butyl (2E)-3-[2-(hydroxymethyl)-4-methylphenyl]acrylate

생성물 1

HCID 86713431tert-butyl (2E)-3-[2-(bromomethyl)-4-methylphenyl]acrylate수율 93.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2.32 g of tert-butyl (2E)-3-[2-(hydroxymethyl)-4-methylphenyl]acrylate in 46 ml of THF were added 4.64 g of carbon tetrabromide and 3.67 g of triphenylphosphine under ice-cooling, followed by stirring at the same temperature for 2.5 hours. To the reaction mixture were added water and ethyl acetate to carry out a layer separation operation. The organic layer was washed with water and saturated brine in this order, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 2.73 g of tert-butyl (2E)-3-[2-(bromomethyl)-4-methylphenyl]acrylate.

후처리

  1. temperaturecooling
  2. customa layer separation operation
  3. washThe organic layer was washed with water and saturated brine in this order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-53f9abb562204188b258f4447111fcd2
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447090B2

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