Benzyl Bromide → 1-Bromo-3-benzyloxy-4,5-difluorobenzene

HRID 602053ノート

反応式

HRID 602053 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([F:9])=[C:6]([OH:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(CC)CC>CCOC(C)=O.O.CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:5]([F:9])=[C:4]([F:10])[CH:3]=1

参加物

8

反応物 4

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 27733075-Bromo-2,3-Difluorophenol

生成物 1

HCID 574706011-Bromo-3-benzyloxy-4,5-difluorobenzene収率 0.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of DMF (100 mL), 5-bromo-2,3-difluorophenol (10 g, 47.85 mol), and K2CO3 (7.27 g, 52.63 mol) and benzyl bromide (9 g, 52.63 mol) were combined at 0° C. under N2. The solution was allowed to warm to rt and stirred overnight. H2O, Et3N (2 eq) and EtOAc (5000 mL) were added and the organic layer separated. The aqueous layer was washed with EtOAc (2×) and the combined organic fractions were washed with 1M HCl (2×), sat. aq. NaHCO3 (2×), dried, and concentrated. The crude product was purified by Biotage (gradient 100% hexanes-60% EtOAc/hexanes) to afford 10.08 g of product as an oil.

後処理

  1. customwere combined at 0° C. under N2
  2. customthe organic layer separated
  3. washThe aqueous layer was washed with EtOAc (2×)
  4. washthe combined organic fractions were washed with 1M HCl (2×), sat. aq. NaHCO3 (2×)
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was purified by Biotage (gradient 100% hexanes-60% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-9499e05c84fc469890fe976704da6dab
出典データセット
uspto-grants-2011_03
特許番号
US07902394B2

反応ノート

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