Phthalimide → 2-(3-(4-Bromophenyl)propyl)isoindoline-1,3-dione

HRID 62036

反応式

HRID 62036 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10]O)=[CH:4][CH:3]=1.[C:12]1(=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[NH:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][N:13]2[C:14](=[O:21])[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12]2=[O:22])=[CH:6][CH:7]=1

参加物

5

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 105606143-(4-Bromophenyl)propan-1-ol

生成物 1

HCID 694934502-(3-(4-Bromophenyl)propyl)isoindoline-1,3-dione

実験手順

To 3-(4-bromophenyl)propan-1-ol (4.70 g, 21.9 mmol), isoindoline-1,3-dione (3.54 g, 24.04 mmol) and triphenylphosphine (6.88 g, 26.2 mmol) in a 500 mL round-bottomed flask equipped with a stir bar, nitrogen, and addition funnel cooled in an ice water bath was added diisopropyl azodicarboxylate (5.10 mL, 26.2 mmol). The reaction was allowed to warm to room temperature over the weekend. The reaction mixture was adsorbed onto Celite®. Purification by flash column chromatography using 5-20% ethyl acetate/hexanes as eluent provided a solid which was dried overnight at 50° C. at about 25 in. Hg providing the title compound as a white solid (6.51 g, 87%): mp 88-90° C.; 1H NMR (400 MHz, CDCl3) δ 7.86-7.79 (m, 2H), 7.71 (dd, J=5.5, 3.0 Hz, 2H), 7.38-7.32 (m, 2H), 7.11-7.04 (m, 2H), 3.73 (t, J=7.1 Hz, 2H), 2.68-2.59 (m, 2H), 2.07-1.96 (m, 2H); ESIMS m/z 346 ([M+2]+).

後処理

  1. additionnitrogen, and addition funnel
  2. temperaturecooled in an ice water bath
  3. customPurification by flash column chromatography
  4. customprovided a solid which
  5. customwas dried overnight at 50° C. at about 25 in

出典と根拠

ORDレコード
ord-203432b332e04f9fb71a438f46d838a7
出典データセット
uspto-grants-2016_09
特許番号
US09445594B2

関連ノート

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