Hydrochloric Acid → 3,3-Bis(fluoromethyl)-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde

HRID 532207노트

반응식

HRID 532207 반응식
[F:1][CH2:2][C:3]1([CH2:14][F:15])[O:7][B:6]([OH:8])[C:5]2[CH:9]=[CH:10][C:11]([CH3:13])=[CH:12][C:4]1=2.C1C(=O)N(Br)C(=[O:19])C1.C([O-])([O-])=O.[Na+].[Na+].Cl>C(Cl)(Cl)(Cl)Cl>[F:1][CH2:2][C:3]1([CH2:14][F:15])[O:7][B:6]([OH:8])[C:5]2[CH:9]=[CH:10][C:11]([CH:13]=[O:19])=[CH:12][C:4]1=2

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 67184N-bromobutanimideHCID 866850763,3-bis(fluoromethyl)-5-methylbenzo[c][1,2]oxaborol-1(3H)-ol

생성물 1

HCID 866850753,3-Bis(fluoromethyl)-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde수율 107.3%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

A solution of 3,3-bis(fluoromethyl)-5-methylbenzo[c][1,2]oxaborol-1(3H)-ol (350 mg, 1.65 mmol), NBS (647 mg, 3.63 mmol), and BPO (40 mg, 0.17 mmol) in CCl4 (10 mL) was refluxed overnight. After treating with aqueous Na2CO3, the aqueous phase was acidified with HCl (3 N) to pH of 3, and then extracted with EA. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product (400 mg) as a yellow solid that was used directly in the next step without purification. 1H NMR (300 MHz, CDCl3): δ 10.09 (s, 1H), 7.98-7.94 (m, 3H), 4.79-4.74 (m, 2H), 4.63-4.59 (m, 2H).

후처리

  1. extractionextracted with EA
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-604e0c15d278473594b1726893b6c9b8
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853186B2

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