Diethyl Ether → HCID 13424426, compound

HRID 462607Notes

Reaction equation

HRID 462607 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].B(Br)(Br)Br.CCOCC>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 25134Boron tribromideHCID 13424425Ethyl 2-(2-methoxyanilino)benzoate

Product 1

HCID 13424426HCID 13424426, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 9.74 g (0.0359 mole) of ethyl 2-(2-methoxyphenylamino)benzoate in 50 ml of methylene dichloride was cooled to -78° C. and 114 ml of boron tribromide (1M in methylene dichloride) was added dropwise over a period of 20 minutes. The reaction mixture was stirred at -78° C. for three hours, then at -40° C. for one hour and finally kept in a refrigerator at -4° C. overnight. Ether (50 ml) was added and the mixture poured into ice-water and ether. The ether solution was separated, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from acetonitrile to give 5.3 g of ethyl 2-(2-hydroxyphenylamino)benzoate, m.p. 105°-106° C.

Workup

  1. waitat -40° C. for one hour
  2. waitfinally kept in a refrigerator at -4° C. overnight
  3. customThe ether solution was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-10d40f4a16054b2ba9b0c8551e6a27a2
Source dataset
uspto-grants-1985_05
Patent number
US04515980

Reaction notes

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