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

HRID 1750827ノート

反応式

HRID 1750827 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dfd984c2e5c740b799ec77dc25b6d657
出典データセット
uspto-grants-2015_10
特許番号
US09156860B2

反応ノート

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