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(4-Chlorophenyl)acetic acid → 1-[5-Bromo-2,3-difluoro-4-(trimethylsilyl)phenyl]-2-(4-chlorophenyl)ethanone

HRID 1879632
ノート
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反応式

HRID 1879632 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=O)=[CH:14][CH:13]=1.[Br:22][C:23]1[C:24]([Si:35]([CH3:38])([CH3:37])[CH3:36])=[C:25]([F:34])[C:26]([F:33])=[C:27]([CH:32]=1)C(OC)=O>C1COCC1.Cl>[Br:22][C:23]1[C:24]([Si:35]([CH3:38])([CH3:37])[CH3:36])=[C:25]([F:34])[C:26]([F:33])=[C:27]([C:19](=[O:21])[CH2:18][C:15]2[CH:14]=[CH:13][C:12]([Cl:11])=[CH:17][CH:16]=2)[CH:32]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 15880(4-Chlorophenyl)acetic acidHCID 2724254Sodium bis(trimethylsilyl)amideHCID 58538053Methyl 5-bromo-2,3-difluoro-4-(trimethylsilyl)benzoate

生成物 1

HCID 585380691-[5-Bromo-2,3-difluoro-4-(trimethylsilyl)phenyl]-2-(4-chlorophenyl)ethanone

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒
HCID 8028
Tetrahydrofuran
溶媒
3 回

実験手順

To a solution of NaHMDS (1.0 M in THF, 7.7 mL, 7.7 mmol) in anhydrous THF (25 mL) at −78° C. was added a solution of 4-chlorophenylacetic acid (0.528 g, 3.09 mmol) in anhydrous THF (25 mL) over 10 minutes. The solution was stirred for 5 minutes, then a solution of the product of Step C (4.16 g, 7.8 mmol) in THF (25 mL) was added drop wise over 10 minutes. The mixture was stirred at −78° C. for two hours. The mixture was diluted with 2N HCl (aq, 50 mL), then the product was extracted into EtOAc. The organics were dried over Na2SO4, filtered, then concentrated. The resulting residue was purified by silica gel chromatography eluting with 0-50% toluene/hexanes to afford the title compound. 1H NMR (600 MHz, CDCl3): δ 7.74 (dd, J=5.3, 1.8 Hz, 1H); 7.31 (d, J=8.2 Hz, 2H); 7.16 (d, J=8.5 Hz, 2H); 4.22 (s, 2H); 0.48 (s, 9H).

後処理

  1. stirringThe mixture was stirred at −78° C. for two hours
  2. extractionthe product was extracted into EtOAc
  3. dry with materialThe organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel chromatography
  7. washeluting with 0-50% toluene/hexanes

出典と根拠

ORDレコード
ord-6eb1d8250863439a848c0c51531978a4
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08318667B2

反応ノート

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