2-Aminophenol → 4-bromo-N-(2-hydroxyphenyl)benzamide

HRID 535231Notes

Reaction equation

HRID 535231 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(N(CC)CC)C.O1CCCC1.[Br:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>O>[Br:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[OH:8])=[O:27])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 58012-AminophenolHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 8310534-bromo-N-(2-hydroxyphenyl)benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

In a 200 mL three-neck flask, 2.2 g (20 mmol) of 2-aminophenol, 3.0 mL (22 mmol) of triethylamine, and 50 mL of tetrahydrofuran (THF) were placed. Then, the mixture was cooled to 0° C. After cooling, 50 mL of a THF solution containing 4.5 g (20 mmol) of 4-bromobenzoyl chloride was dripped under nitrogen stream. This solution was stirred at 0° C. for 4 hours under nitrogen stream. After a certain period, the solution was added to water, and an aqueous layer was extracted with ethyl acetate. The resulting extracted solution and the organic layer were combined and washed with 0.2 M hydrochloric acid and a saturated aqueous solution of sodium hydrogen carbonate, and then the organic layer was dried with magnesium sulfate. The mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and the filtrate was condensed to give a solid. The solid was recrystallized with ethyl acetate/hexane, so that 5.3 g of target white powder was obtained in a yield of 88%.

Workup

  1. temperatureAfter cooling
  2. waitAfter a certain period
  3. extractionan aqueous layer was extracted with ethyl acetate
  4. extractionThe resulting extracted solution
  5. washwashed with 0.2 M hydrochloric acid
  6. dry with materiala saturated aqueous solution of sodium hydrogen carbonate, and then the organic layer was dried with magnesium sulfate
  7. filtrationThe mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855)
  8. customcondensed
  9. customto give a solid
  10. customThe solid was recrystallized with ethyl acetate/hexane, so that 5.3 g of target white powder
  11. customwas obtained in a yield of 88%

Sources & evidence

ORD record
ord-d4ba2002b40f43ee99cf623683b9db21
Source dataset
uspto-grants-2014_10
Patent number
US08859108B2

Reaction notes

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