Ammonium Hydroxide → 4-(2-Bromotetrafluoroethoxy)benzamide

HRID 1493539Notes

Reaction equation

HRID 1493539 reaction equation
[Br:1][C:2]([F:17])([F:16])[C:3]([F:15])([F:14])[O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1.[OH-].[NH4+:19]>>[Br:1][C:2]([F:17])([F:16])[C:3]([F:15])([F:14])[O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH2:19])=[O:10])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 19763911HCID 19763911, compound

Product 1

HCID 197639074-(2-Bromotetrafluoroethoxy)benzamideYield 99%

Procedure

4-(2-Bromotetrafluoroethoxy)benzoic acid prepared as in Example 18 (26.6 g, 0.083 mol) is transferred to a 250 mL round-bottomed flask along with 150 mL of methylene chloride. Oxalyl chloride (11.64 g, 0.92 mol) is added and the mixture is stirred under nitrogen overnight to form a turbid solution which is concentrated by rotary evaporation and distilled at 80°-90° C./0.1 mmHg to yield 20.88 g of 4(2-bromotetrafluoroethoxy)benzoyl chloride as a colorless liquid, leaving 6.16 g of unreacted acid (76.8% conversion, 96.5% yield). The benzoyl chloride is added slowly with stirring to 8 mL of cold ammonium hydroxide (0.12 mol). The product amide precipitates as fine white needles which are filtered and dried under vacuum to yield 14.74 g of 4-(2-bromotetrafluoroethoxy)benzamide (75% conversion, 99% yield, m p. 150.5°-151.5° C.), along with 4.8 g of 4-(2-bromotetrafluoroethoxy)benzoic acid which is recovered from the mother liquor (24.3% recovery).

Workup

  1. customThe product amide precipitates as fine white needles which
  2. filtrationare filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-f7510ee501ca485e955036cf5f234d3b
Source dataset
uspto-grants-1991_06
Patent number
US05021602

Reaction notes

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