Phosphorus oxychloride → 7-Benzyloxy-6-bromo-4-chloro-2-methyl-quinoline

HRID 1006175Notes

Reaction equation

HRID 1006175 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](O)=[CH:14][C:15]([CH3:19])=[N:16]2)=[CH:11][C:10]=1[Br:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:24])=O>>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:24])=[CH:14][C:15]([CH3:19])=[N:16]2)=[CH:11][C:10]=1[Br:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1784287967-Benzyloxy-6-bromo-2-methyl-quinolin-4-ol

Product 1

HCID 220545547-Benzyloxy-6-bromo-4-chloro-2-methyl-quinolineYield 86.6%

Procedure

7-Benzyloxy-6-bromo-2-methyl-quinolin-4-ol (25.0 g, 72.6 mmol) and phosphorous oxychloride (70 mL, 0.764 mol) were heated 40 min at 130° C. and then cooled down to room temperature. Phosphorous oxychloride was evaporated under high vacuum. Ice water was added and the pH of this solution was adjusted to 9 with ammonium hydroxide. The suspension was extracted with dichloromethane. The combined organic layers were dried under vacuum. 22.8 g of the title compound were obtained. Brown solid, ISP-MS: m/e=364.0 ([M+H]+).

Workup

  1. customPhosphorous oxychloride was evaporated under high vacuum
  2. additionIce water was added
  3. extractionThe suspension was extracted with dichloromethane
  4. customThe combined organic layers were dried under vacuum

Sources & evidence

ORD record
ord-b950ed5933c24f2db0b84a05d7a6add8
Source dataset
uspto-grants-2004_09
Patent number
US06787558B2

Reaction notes

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