Methanol → Phenol, 4-(diphenylamino)-

HRID 525986Notes

Reaction equation

HRID 525986 reaction equation
C[O:2][C:3]1[CH:21]=[CH:20][C:6]([N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.CO.O>C(Cl)Cl>[C:8]1([N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6]2[CH:20]=[CH:21][C:3]([OH:2])=[CH:4][CH:5]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25134Boron tribromideHCID 98820374-Methoxytriphenylamine

Product 1

HCID 11492641Phenol, 4-(diphenylamino)-Yield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxy-N,N-diphenylaniline (6.0 g, 21.8 mmol) in DCM (40 mL) was slowly added BBr3 (23 mL, 23 mmol) at about −78° C. The mixture was then stirred overnight under argon while it slowly warmed up to room temperature. To the resulting mixture, methanol (70 mL) was added slowly, then stirred for about 3 hours. The mixture was then poured into water and extracted with DCM (2×200 mL). The organic phases were then combined and washed with brine, dried over Na2SO4, loaded on silica gel, and purified by short plug using hexane/ethyl acetate (9:1 to 8:1). The desired fraction was concentrated and washed with hexanes to give a white solid (Compound 7) (4.59 g, in 81% yield).

Workup

  1. customat about −78° C
  2. stirringstirred for about 3 hours
  3. extractionextracted with DCM (2×200 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. custompurified by short plug
  7. concentrationThe desired fraction was concentrated
  8. washwashed with hexanes

Sources & evidence

ORD record
ord-a237686e1aa24a96b17c9d69cb0d8bb6
Source dataset
uspto-grants-2016_05
Patent number
US09343684B2

Reaction notes

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