Hydrochloric Acid → 4-(Benzyloxy)-2-vinylphenylboronic acid

HRID 860707ノート

反応式

HRID 860707 の反応式
[B:1](OC(C)C)([O:6]C(C)C)[O:2]C(C)C.[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25](Br)=[C:24]([CH:29]=[CH2:30])[CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([Li])CCC.Cl>C1COCC1.O>[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([B:1]([OH:6])[OH:2])=[C:24]([CH:29]=[CH2:30])[CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 692072164-(Benzyloxy)-1-bromo-2-vinylbenzeneHCID 178418339Butyllithium

生成物 1

HCID 692054944-(Benzyloxy)-2-vinylphenylboronic acid収率 602.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Triisopropyl borate (683 mg, 3.63 mmol) was added to a stirred solution of 4-(benzyloxy)-1-bromo-2-vinylbenzene (1.0 g, 0.346 mmol) in THF (9 mL). The solution was cooled in a CO2/acetone bath. A solution of n-butyllithium (1.45 mL of 2.5M in hexanes, 3.63 mmol) was added dropwise over 5 minutes. The cooling bath was left in place and was allowed to warm to room temperature. The mixture was treated with HCl (5 mL of 1N) and water (5 mL), stirred for 1 hour, and extracted with ethyl acetate (3×15 mL). The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated to an oil which crystallized from diethyl ether/hexanes to provide colorless crystals of the desired product (530 mg, 57% yield). 1H NMR (300 MHz, CDCl3) δ 5.14 (s, 2H), 5.34 (d, J=12.44 Hz, 1H), 5.68 (d, J=17.57 Hz, 1H), 6.97 (dd, J=8.42, 2.56 Hz, 1H), 7.36 (m, 6H), 7.83 (dd, J=17.57, 10.98 Hz, 1H), 8.16 (d, J=8.42 Hz, 1H).

後処理

  1. temperatureThe solution was cooled in a CO2/acetone bath
  2. waitThe cooling bath was left in place
  3. extractionextracted with ethyl acetate (3×15 mL)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to an oil which
  8. customcrystallized from diethyl ether/hexanes

出典と根拠

ORDレコード
ord-369bb6ac04cd48e59e3dd195ae4c3b7a
出典データセット
uspto-grants-2006_12
特許番号
US07153848B2

反応ノート

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