2-(2-Benzoxazolyl)phenol → HCID 67072674, compound

HRID 1506817

Reaction equation

HRID 1506817 reaction equation
C1(B([O:14][B:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)C2C=CC=CC=2)C=CC=CC=1.O[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35]1[O:36][C:37]2[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=2[N:39]=1>O1CCCC1>[C:22]1([B:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[O:14][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]2[O:36][C:37]3[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=3[N:39]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 132692-(2-Benzoxazolyl)phenolHCID 596810Diphenylborinic anhydride

Product 1

HCID 67072674HCID 67072674, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diphenylborinic anhydride (5.0 g; 0.014 mole) in tetrahydrofuran (20 ml) was added to a solution of 2-(2′-hydroxyphenyl)benzoxazole (3.1 g; 0.014 mole) in tetrahydrofuran (10 ml). The reaction mixture was refluxed under nitrogen for 2 h and allowed to cool to room temperature, then kept in the refrigerator for 18 h. The product was filtered off under suction, washed with methanol and dried under vacuum at 80° C. for 6 h. Yield 4.4 g (84%). The product was further purified by sublimation (85%). M.p 195° C. (DSC, onset); Tg 59° C. Elemental analysis:

Workup

  1. temperatureThe reaction mixture was refluxed under nitrogen for 2 h
  2. filtrationThe product was filtered off under suction
  3. washwashed with methanol
  4. customdried under vacuum at 80° C. for 6 h
  5. customThe product was further purified by sublimation (85%)
  6. customM.p 195° C. (DSC, onset)

Sources & evidence

ORD record
ord-0c15ac0549a74bb9b8ae73caa55a46a3
Source dataset
uspto-grants-2015_12
Patent number
US09221770B2

Linked notes

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