Boron tribromide → 4-(1,2,3,4-Tetrahydro-acridin-9-yl)-phenol

HRID 2251100Notes

Reaction equation

HRID 2251100 reaction equation
B(Br)(Br)Br.C([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]3[C:25]([N:26]=[C:27]4[C:32]=2[CH2:31][CH2:30][CH2:29][CH2:28]4)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=1)C1C=CC=CC=1>C(Cl)Cl>[CH2:31]1[C:32]2[C:27](=[N:26][C:25]3[C:20]([C:19]=2[C:16]2[CH:17]=[CH:18][C:13]([OH:12])=[CH:14][CH:15]=2)=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:28][CH2:29][CH2:30]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58587702HCID 58587702, compound

Product 1

HCID 1360572454-(1,2,3,4-Tetrahydro-acridin-9-yl)-phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

BBr3 (3.2 mL, 1 M solution in CH2Cl2, 3.2 mmol) was added dropwise to a stirred solution of 9-(4-benzyloxy-phenyl)-1,2,3,4-tetrahydro-acridine (0.23 g 0.64 mmol) in CH2Cl2 (3 mL) at 0° C. The resulting mixture was warmed to room temperature over a period of 3 hours followed by dilution with CH2Cl2 (50 mL). The solution was washed with sat. aq. NaHCO3 until aq. washings were basic (pH˜9). The CH2Cl2 layer was dried over Na2SO4, decanted and concentrated. The residue was washed with hexanes (2×10 mL) and decanted to remove benzyl bromide. The resulting product was used without further purification.

Workup

  1. washThe solution was washed with sat. aq. NaHCO3 until aq. washings
  2. dry with materialThe CH2Cl2 layer was dried over Na2SO4
  3. customdecanted
  4. concentrationconcentrated
  5. washThe residue was washed with hexanes (2×10 mL)
  6. customdecanted
  7. customto remove benzyl bromide
  8. customThe resulting product was used without further purification

Sources & evidence

ORD record
ord-59bc4903a4cc474a8ef5fc009350a9b6
Source dataset
uspto-grants-2008_01
Patent number
US07319103B2

Reaction notes

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