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

HRID 264597

反応式

HRID 264597 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 rain, 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 solid: 1H NMR (400 MHz, DMSO-d6) δ0.89 (t, 3H, J=7.2 Hz), 1.38 (m, 4H), 1.72 (m, 2H), 3.99 (t, 2H, 1-6.5Hz), 6.99 (d, 2H, J=8.8 Hz), 7.57 (d, 2H, J=8.2 Hz), 7.60 (d, 2H, J=8.8 Hz), 7.83 (d, 2H, J=8.2 Hz).

後処理

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

出典と根拠

ORDレコード
ord-795bc943dcb3460594dfe3d775cf1ec5
出典データセット
uspto-grants-1997_07
特許番号
US05646245

関連ノート

読み込み中…