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

HRID 439700

반응식

HRID 439700 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 113580714'-Pentyloxybiphenyl-4-boronic Acid수율 84.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-29d1296b53a4438d9b7086e9a61b7440
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05516756

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