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

HRID 1037137ノート

反応式

HRID 1037137 の反応式
[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

参加物

3

反応物 2

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

生成物 1

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

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e3cac0e834dd41e1a76f0a09988b616f
出典データセット
uspto-grants-2013_10
特許番号
US08546357B2

反応ノート

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