tert-Butanol → tert-butyl N-(5-bromo-2-chlorophenyl)carbamate

HRID 1803604

反応式

HRID 1803604 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:19])C=CC=CC=1.CC[N:31]([CH2:34]C)CC.[C:36]([OH:40])([CH3:39])([CH3:38])[CH3:37]>>[C:36]([O:40][C:34](=[O:19])[NH:31][C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[Cl:11])([CH3:39])([CH3:38])[CH3:37]

参加物

5

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 331275-Bromo-2-chlorobenzoic acidHCID 199401P,P-Diphenylphosphinic azide

生成物 1

HCID 57840526tert-butyl N-(5-bromo-2-chlorophenyl)carbamate

実験手順

A solution of 5-Bromo-2-Chloro benzoic acid (24 g, 0.1 mol), di-phenylphosphoryl azide (28 mL, 1.3 eq), and Et3N (140 mL, 10 eq) in tert-butanol (300 mL) was refluxed for 3 hrs. The resulting solution was concentrated under reduced pressure, diluted with ether (300 mL) and washed with HCl 1N (300 mL), saturated solution of NaHCO3 (200 mL), and brine (200 mL). The organic layers was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/n-hexane) yielded, (26 g, 85%).

後処理

  1. concentrationThe resulting solution was concentrated under reduced pressure
  2. additiondiluted with ether (300 mL)
  3. washwashed with HCl 1N (300 mL), saturated solution of NaHCO3 (200 mL), and brine (200 mL)
  4. dry with materialThe organic layers was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customChromatography on silica (EtOAc/n-hexane) yielded

出典と根拠

ORDレコード
ord-c568271e01884979a91252abcd2887f4
出典データセット
uspto-grants-2013_01
特許番号
US08349836B2

関連ノート

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