1,3-Dibromobenzene → 3-Bromo-3'-vinylbiphenyl

HRID 1043429ノート

反応式

HRID 1043429 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:15]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)=[CH2:16]>COCCOC.O>[Br:8][C:4]1[CH:3]=[C:2]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:15]=[CH2:16])[CH:22]=2)[CH:7]=[CH:6][CH:5]=1

参加物

6

反応物 3

HCID 79271,3-DibromobenzeneHCID 11430Potassium CarbonateHCID 43668863-Vinylphenylboronic Acid (contains varying amounts of Anhydride)

生成物 1

HCID 592665703-Bromo-3'-vinylbiphenyl収率 60%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

A solution of 1,3-dibromobenzene (5.3 mL, 43.9 mmol), potassium carbonate (14.0 g, 101 mmol) and 3-vinylphenylboronic acid (5 g, 33.8 mmol) in DME (100 mL) and water (20 mL) (in a pressure vessel) was sparged with nitrogen for 15 min. Pd(PPh3)3 (1.17 g, 1.014 mmol) was added and then the reaction was heated to 80° C. overnight. The reaction was cooled to r.t. and evaporated on the rotovap. The residue was diluted in EtOAc and washed with water then brine, dried over MgSO4, filtered and evaporated to give the crude material. The crude material was purified by flash chromatography on the Biotage (0-5% EtOAc:Hex) to give 3-bromo-3′-vinylbiphenyl (5.21 g, 20.10 mmol, 60% yield) as a clear liquid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.33 (d, J=10.79 Hz, 1H) 5.84 (dd, J=17.57, 0.75 Hz, 1H) 6.80 (dd, J=17.57, 10.79 Hz, 1H) 7.32 (t, J=7.78 Hz, 1H) 7.38-7.48 (m, 3H) 7.51 (dddd, J=13.24, 7.84, 1.76, 1.00 Hz, 2H) 7.56-7.61 (m, 1H) 7.76 (t, J=1.88 Hz, 1H).

後処理

  1. temperatureThe reaction was cooled to r.t.
  2. customevaporated on the rotovap
  3. additionThe residue was diluted in EtOAc
  4. washwashed with water
  5. dry with materialbrine, dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give the crude material
  9. customThe crude material was purified by flash chromatography on the Biotage (0-5% EtOAc:Hex)

出典と根拠

ORDレコード
ord-ccae06a7d45b488fb54190fb3a1e0423
出典データセット
uspto-grants-2013_10
特許番号
US08563505B2

反応ノート

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