Nitric Acid → 4-Bromomethyl-3-nitrobenzoic acid

HRID 461300

反応式

HRID 461300 の反応式
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.[N+:12]([O-])([OH:14])=[O:13]>>[N+:12]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:3]=1[CH2:2][Br:1])[C:9]([OH:11])=[O:10])([O-:14])=[O:13]

参加物

3

反応物 2

HCID 944Nitric AcidHCID 225994-(Bromomethyl)benzoic acid

生成物 1

HCID 1323864-Bromomethyl-3-nitrobenzoic acid収率 85%

実験手順

The bromoacid 3 (11.8 g) was added in portions over 0.5 hour to 100 ml of 90% HNO3 (white fumming) at -10° C. The suspension was stirred at -10° for an additional 2 hours when the solution became clear orange. This solution was poured onto crushed ice. The product was collected by filtration, washed with ice cold H2O (3 × 50 ml) until the washings were neutral. Drying in vacuo followed by crystallization twice from CH2Cl2 /hexane gave pure nitro acid 4 (11.02 g, 85%): m.p. 125-126, i.r. (Nujol) 2800-2300, 1690, 1610 (COOH), 1600 (Aromatic), 1540, 1300 cm-1 (NO2); nmr (CDCl3, DMSO-d6) 4.9 (S,2), 7.8 (d,1), 8.2 (dd,1), 8.6 (d,1) 10.8 (s,1); Rf(5) 0.55; Rf (1) 0.82; UVmax (CH3OH) 227 mμ (t = 2.13 104) 305 mμ (t 4.1 × 103).

後処理

  1. additionThis solution was poured
  2. customonto crushed ice
  3. filtrationThe product was collected by filtration
  4. washwashed with ice cold H2O (3 × 50 ml) until the washings
  5. customDrying in vacuo
  6. customfollowed by crystallization twice from CH2Cl2 /hexane

出典と根拠

ORDレコード
ord-5ab3fc49b9144112ba9701946dae909f
出典データセット
uspto-grants-1977_12
特許番号
US04062746

関連ノート

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