Hydrochloric Acid → 2-Chloro-4-ethoxyphenylboronic Acid (contains varying amounts of Anhydride)

HRID 51022노트

반응식

HRID 51022 반응식
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[CH:9][C:8]=1[Cl:16].C[O:18][B:19](OC)[O:20]C.Cl>C1COCC1>[Cl:16][C:8]1[CH:9]=[C:10]([O:13][CH2:14][CH3:15])[CH:11]=[CH:12][C:7]=1[B:19]([OH:20])[OH:18]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 227356231-Bromo-2-chloro-4-ethoxybenzeneHCID 178418339Butyllithium

생성물 1

HCID 35397162-Chloro-4-ethoxyphenylboronic Acid (contains varying amounts of Anhydride)

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

n-Butyllithium (1.6 M solution in hexanes, 23.5 mmol, 14.7 mL) was added to l-bromo-2-chloro-4-ethoxybenzene (19.5 mmol, 4.59 g) in THF (120 mL) at −78° C. under an atmosphere of nitrogen. After stirring for thirty minutes the trimethylborate (76.6 mmol, 8.7 mL) was added over twenty minutes. The reaction was allowed to warm to room temperature overnight while stirring. The solution was then acidified with HCl (3 M, 200 mL), and extracted into EtOAc. The EtOAc was then extracted with NaOH (1 N, 4×100 mL), which was subsequently acidified with concentrated HCl forming a white precipitate. The white precipitate (2.25 g, 58%) was filtered and dried to afford (2-Chloro-4-ethoxyphenyl)boronic acid. 1H NMR (CDCl3, 300 MHz): 7.87 (1H, d, J 8.4 Hz), 6.88 (1H, d, J 2.5 Hz), 6.84 (1H, dd, J 8.4 and 2.5 Hz), 5.53 (2H, br. s), 4.06 (2H, q, J 7.07 Hz), 1.42 (3H, t, J 7.0 Hz.)

후처리

  1. additionwas added over twenty minutes
  2. extractionextracted into EtOAc
  3. extractionThe EtOAc was then extracted with NaOH (1 N, 4×100 mL), which
  4. filtrationThe white precipitate (2.25 g, 58%) was filtered
  5. customdried

출처 및 근거

ORD 기록
ord-7144339e7f3a4c2e8a6c7d3d8a364712
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713471B1

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