Hydrochloric Acid → 4'-Pentyloxybiphenyl-4-boronic Acid

HRID 439700

反応式

HRID 439700 の反応式
[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C([Li])CCC.C([O:28][B:29](OC(C)C)[O:30]C(C)C)(C)C.Cl>O1CCCC1>[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([B:29]([OH:30])[OH:28])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 28013884-Bromo-4'-(pentyloxy)-1,1'-biphenylHCID 178418339Butyllithium

生成物 1

HCID 113580714'-Pentyloxybiphenyl-4-boronic Acid収率 84.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a stirred suspension of 4-(4-n-pentoxyphenyl)bromobenzene (1.0 g, 3.13 mmol) in anhydrous tetrahydrofuran (20 ml) at -78° C. under a nitrogen atmosphere was added n-butyllithium in hexanes (2.5M, 1.32 ml, 3.30 mmol). After a period of 15 min, triisopropylborate (760 μl, 3.30 mmol) was added. Stirring at -78° C. was continued for 15 min and then at 25° C. for 40 min. The mixture was acidified with 0.5N HCl (20 mL) and then partitioned between ether (50 ml) and water (40 ml). The organic phase was washed with water (3×) and brine and dried with magnesium sulfate. The solvent was removed in vacuo to give 4-(4-n-pentoxyphenyl)phenylboronic acid (750 mg) as a white solid: 1H NMR (400 MHZ, DMSO-d6) δ 0.89 (t, 3, J=7.2 Hz), 1.38 (m, 4 ), 1.72 (m, 2), 3.99 (t, 2, J=6.5 Hz), 6.99 (d, 2, J=8.8 Hz), 7.57 (d, 2, J=8.2 Hz), 7.60 (d, 2, J=8.8 Hz), 7.83 (d, 2, J=8.2 Hz).

後処理

  1. waitwas continued for 15 min
  2. waitat 25° C. for 40 min
  3. custompartitioned between ether (50 ml) and water (40 ml)
  4. washThe organic phase was washed with water (3×) and brine
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-29d1296b53a4438d9b7086e9a61b7440
出典データセット
uspto-grants-1996_05
特許番号
US05516756

関連ノート

読み込み中…