N-bromobutanimide → Bromoadamantylideneadamantane

HRID 247153

反応式

HRID 247153 の反応式
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[C:11]1[CH:18]3[CH2:19][CH:14]4[CH2:15][CH:16]([CH2:20][CH:12]1[CH2:13]4)[CH2:17]3)[CH2:8]2.[Br:21]N1C(=O)CCC1=O>C(Cl)Cl>[Br:21][C:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[C:2]1=[C:11]1[CH:12]3[CH2:20][CH:16]4[CH2:15][CH:14]([CH2:19][CH:18]1[CH2:17]4)[CH2:13]3)[CH2:10]2

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 141567Biadamantylidene

生成物 1

HCID 70517409Bromoadamantylideneadamantane

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3 mmols (804 mg) adamantylideneadamantane in 40 cm3CH2Cl2, 6.6 mmols (1.175 g) N-bromosuccinimide was added. The reaction mixture was refluxed and stirred for 12 hours. The reaction mixture was diluted with CH2Cl2 and washed twice with water and a saturated Na2S3O3 -solution. The organic layer was dried with MgSO4 and evaporated. The yield of 4-eq.-bromoadamantylideneadamantane having formula 20 was 1.05 g (97%). An analytically pure sample could be obtained by crystallization from acetone and sublimation (115° C./0.002 mm); melting point 130.5-131.5° C. 1H NMR (CDCl3); δ 4.4 (br s, 1H); 3.05 (br s, 1H); 2.8 (br s, 3H); 2.6-1.2 (br m, 22H); 13C NMR (CDCl3); δ 136.9 (s); 131.0 (s); 63.8 (d) and 12 signals between 39.9 and 27.6. Analysis, calculated: 69.16 C; 7.84 H; 23.01 Br; found: 69.21 C; 7.82 H; 22.99 Br. Mass m/e 346:348 (1:1).

後処理

  1. temperatureThe reaction mixture was refluxed
  2. washwashed twice with water
  3. dry with materialThe organic layer was dried with MgSO4
  4. customevaporated
  5. customAn analytically pure sample could be obtained by crystallization from acetone and sublimation (115° C./0.002 mm)

出典と根拠

ORDレコード
ord-0ba26287e1504169ac16a685e516d48c
出典データセット
uspto-grants-1987_11
特許番号
US04705847

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