Hydrochloric Acid → (4-Cyclopropoxyphenyl)boronic acid

HRID 646152ノート

反応式

HRID 646152 の反応式
Br[C:2]1([O:8][CH:9]2[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH2:3]1.[Li]CCCC.[B:17](OCC)([O:21]CC)[O:18]CC.Cl>C1COCC1>[CH:9]1([O:8][C:2]2[CH:7]=[CH:6][C:5]([B:17]([OH:21])[OH:18])=[CH:4][CH:3]=2)[CH2:11][CH2:10]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 9009Triethyl borateHCID 686990414-Bromo-4-cyclopropoxybenzeneHCID 178418339Butyllithium

生成物 1

HCID 53216708(4-Cyclopropoxyphenyl)boronic acid収率 36%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-bromo-4-cyclopropoxybenzene (5.0 g, 23.4 mmol, see Example 39(c)) in THF (80 mL) at −78° C. was added n-BuLi (2.5 M solution in hexane; 9.76 mL, 24.4 mmol) over 17 min. After 40 min, B(OEt)3 (5.9 mL, 34.3 mmol) was added and the reaction was warmed to room temperature and stirred at ambient temperature for 18 h. After re-cooling to 0° C., HCl (1M solution; 70 mL, aq.) was added. After 30 min the mixture was extracted with t-BuOMe (3×50 mL), the combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was washed with light petrol and filtered yielding the sub-title compound (1.5 g, 34%).

後処理

  1. temperatureAfter re-cooling to 0° C.
  2. extractionAfter 30 min the mixture was extracted with t-BuOMe (3×50 mL)
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. washThe residue was washed with light petrol
  7. filtrationfiltered

出典と根拠

ORDレコード
ord-821109ee1aad4d8490dc0337242d8313
出典データセット
uspto-grants-2010_04
特許番号
US07705023B2

反応ノート

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