Ethyl bromoacetate → HCID 54094066、化合物

HRID 580955ノート

反応式

HRID 580955 の反応式
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:8]([C:11]1[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:12]=1[OH:18])[CH:9]=[CH2:10].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:8]([C:11]1[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:12]=1[O:18][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:9]=[CH2:10]

参加物

5

反応物 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 2584682-ALLYL-4-BROMOPHENOL

生成物 1

HCID 54094066HCID 54094066、化合物収率 70.2%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

Ethyl bromoacetate (1.68 g) was added to a stirred suspension of 2-allyl-4-bromophenol (2.13 g) and potassium carbonate (1.50 g) in butan-2-one (15 ml). The mixture was heated at reflux for 16 hours. The reaction mixture was cooled to ambient temperature and filtered. Water (100 ml) was added to the filtrate and the aqueous phase was extracted with ethyl acetate (3×50 ml). The ethyl acetate extracts were combined, washed with brine (2×25 ml), dried (MgSO4) and evaporated to give a solid which crystallised from hexane to give ethyl 2-allyl-4-bromophenoxyacetate (2.10 g), mp 70.5° C.; microanalysis, found: C, 52.0; H, 5.10%; C13H15BrO3 requires: C, 52.2; H, 5.05%; NMR (CDCl3) 1.29 (3H, t), 3.42 (2H, d), 4.25 (2H, q), 4.58 (2H, s), 5.07-5.17 (2H, m), 5.88-6.18 (1H, m), 6.60 (1H, d) and 7.20-7.27 (2H, m); m/z 300 (M+H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 hours
  3. filtrationfiltered
  4. additionWater (100 ml) was added to the filtrate
  5. extractionthe aqueous phase was extracted with ethyl acetate (3×50 ml)
  6. washwashed with brine (2×25 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customto give a solid which
  10. customcrystallised from hexane

出典と根拠

ORDレコード
ord-a6ec198392534efd95a6b4c0de2e5dda
出典データセット
uspto-grants-1999_07
特許番号
US05919793

反応ノート

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