2-(Benzyloxy)-5-fluorobenzonitrile → 5-Fluoro-2-hydroxybenzonitrile

HRID 1665987노트

반응식

HRID 1665987 반응식
C([O:8][C:9]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:10]=1[C:11]#[N:12])C1C=CC=CC=1>CO>[F:17][C:14]1[CH:15]=[CH:16][C:9]([OH:8])=[C:10]([CH:13]=1)[C:11]#[N:12]

참가 물질

3

반응물 1

HCID 582814722-(Benzyloxy)-5-fluorobenzonitrile

생성물 1

HCID 129192915-Fluoro-2-hydroxybenzonitrile수율 106%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Dry 10% Pd/C (2.48 g) was placed in a 5 L flask under N2. A solution of 2-(benzyloxy)-5-fluorobenzonitrile (148 g, 651 mmol) in methanol (2.34 L) was added slowly under N2. The air of the flask was removed by vacuum and the flask was charged with H2 (balloon) three times. The mixture was stirred at room temperature for 1 hour. The above process was repeated two more times to push the reaction to completion. The mixture was stirred at room temperature for another 2 hours. The mixture was filtered through a Celite pad under N2 and washed with EtOAc (150 mL×2). The palladium waste was rinsed with water (50 mL) and discarded. The filtrates were concentrated to give (94.6 g, 106%) of the desired compound as a yellow solid. MS (APCI-) m/z 137 (M−1) was detected. 1H NMR (400 MHz, DMSO-d6) δ 11.07 (br, 1H), 7.58 (dd, 1H, J=3.2 Hz, J=8.2 Hz), 7.43 (m, 1H), 6.91-7.03 (dd, 1H J=4.5 Hz, J=9.2 Hz).

후처리

  1. dry with materialDry 10% Pd/C (2.48 g)
  2. customwas placed in a 5 L flask under N2
  3. customThe air of the flask was removed by vacuum
  4. additionthe flask was charged with H2 (balloon) three times
  5. customthe reaction to completion
  6. stirringThe mixture was stirred at room temperature for another 2 hours
  7. filtrationThe mixture was filtered through a Celite pad under N2
  8. washwashed with EtOAc (150 mL×2)
  9. washThe palladium waste was rinsed with water (50 mL)
  10. concentrationThe filtrates were concentrated

출처 및 근거

ORD 기록
ord-96dfe1f4fe8a4a929a7ec55259b595c2
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039639B2

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