Hydrochloric Acid → 4-fluoro-3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol

HRID 1037137노트

반응식

HRID 1037137 반응식
[F:1][C:2]1[C:3]([C:18]([O:21]COC)([CH3:20])[CH3:19])=[C:4]([B:9]2[O:13]C(C)(C)C(C)(C)O2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.Cl>>[F:1][C:2]1[C:3]2[C:18]([CH3:19])([CH3:20])[O:21][B:9]([OH:13])[C:4]=2[CH:5]=[C:6]([CH3:8])[CH:7]=1

참가 물질

3

반응물 2

HCID 313Hydrochloric AcidHCID 866855012-(3-Fluoro-2-(2-(methoxymethoxy)propan-2-yl)-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 866855004-fluoro-3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol수율 52.5%

실험 절차

The crude 2-(3-fluoro-2-(2-(methoxymethoxy)propan-2-yl)-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was mixed with 25 ml of 6N HCl and the reaction mixture was stirred at rt overnight. The reaction was monitored by LC-MS. The reaction solution was extracted with EtOAc, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE-EA (5:1 to 2:1) to give 4-fluoro-3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol (3.5 g, 52.5% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 9.17 (s, 1H), 7.30 (s, 1H), 7.08 (d, J=11.2 Hz, 1H), 2.34 (s, 3H), 1.49 (s, 6H) ppm.

후처리

  1. extractionThe reaction solution was extracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography over silica gel
  6. washeluted with PE-EA (5:1 to 2:1)

출처 및 근거

ORD 기록
ord-e3cac0e834dd41e1a76f0a09988b616f
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546357B2

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