Sodium Carbonate → 5-Bromo-6-(4-fluorophenyl)-1,3-benzodioxole

HRID 1598844ノート

反応式

HRID 1598844 の反応式
Br[C:2]1[C:10]([Br:11])=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:11][C:10]1[C:2]([C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)=[CH:3][C:4]2[O:8][CH2:7][O:6][C:5]=2[CH:9]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 2258145,6-Dibromo-1,3-dioxaindaneHCID 2856454-Fluorophenylboronic acid

生成物 1

HCID 234510685-Bromo-6-(4-fluorophenyl)-1,3-benzodioxole収率 71.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

Under nitrogen, 1.1 g of Pd(PPh3)4 was added to a stirred solution of 10.4 g (37.2 mmol) of 5,6-dibromo-1,3-benzodioxole and 2.6 g (18.6 mmol) of 4-fluorophenylboronic acid in 100 mL of toluene, 60 mL of ethanol, and 40 mL of M Na2CO3. After vigorous stirring at reflux overnight, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate, washed with water, and dried over Na2 SO4. Purification by silica gel chromatography (Waters Prep-500A) with hexane as the eluent gave 3.9 g (71%) of 5-bromo-6 (4-fluorophenyl)-1,3-benzodioxole as a colorless solid: mp 86.0°-87.5° C.; NMR (CDCl3) δ 6.02 (s, H), 6.77 (s, 1H), 7.04-7.13 (m, 3H), 7.28-7.35 (m, 2H).

後処理

  1. temperatureat reflux overnight
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. customdried over Na2 SO4
  6. customPurification by silica gel chromatography (Waters Prep-500A) with hexane as the eluent

出典と根拠

ORDレコード
ord-e319f95d97134e2aa2a0a61c339112c3
出典データセット
uspto-grants-1998_04
特許番号
US05739166

反応ノート

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