Carbon tetrabromide → 1,1'-Biphenyl, 4-(3-bromopropoxy)-

HRID 459152Notes

Reaction equation

HRID 459152 reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][CH2:9][CH2:10]O)=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:38]>C(Cl)Cl>[Br:38][CH2:10][CH2:9][CH2:8][O:7][C:4]1[CH:5]=[CH:6][C:1]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 283517393-(4-Phenylphenoxy)-1-propanol

Product 1

HCID 152334631,1'-Biphenyl, 4-(3-bromopropoxy)-Yield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(biphenyl-4-yloxy)-propan-1-ol (1.00 g, 4.38 mmol) in CH2Cl2 (20 mL) at 0° C. was added triphenylphosphine (1.61 g, 6.14 mmol) and carbon tetrabromide (1.81 g, 5.47 mmol). The reaction mixture was allowed to warm to room temperature, stirred for 1 hour, and extracted with ethyl acetate (50 mL). The organic layer was washed with H2O (3×50 mL) and bine (3×25 mL), dried (MgSO4), filtered and concentrated. The crude product was purified by silica gel column chromatography (silica gel, hexanes/ethyl acetate, 9:1) to produce 4-(3-bromo-propoxy)-biphenyl (1.22 g, 95%). 1H-NMR (200.15 MHz, CDCl3): δ 7.57–7.29 (m, 7H), 6.98 (dd, 2H, J=6.72, 1.88), 4.15 (t, 2H, J=5.92), 3.62 (t, 2H, J=6.44), 2.34 (qn, 2H, J=5.92).

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. washThe organic layer was washed with H2O (3×50 mL) and bine (3×25 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel column chromatography (silica gel, hexanes/ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-514ce74530a34d9ebe2803419a230e3a
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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