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

HRID 459315Notes

Reaction equation

HRID 459315 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29]O)=[CH:22][CH:21]=1.C(Br)(Br)(Br)[Br:38]>C(Cl)Cl>[Br:38][CH2:29][CH2:28][CH2:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (1.61 g, 6.14 mmol) was added to a solution of 3-(biphenyl-4-yloxy)-propan-1-ol (Example 291, Step 6) (1.00 g, 4.38 mmol) and carbon tetrabromide (1.81 g, 5.47 mmol) in CH2Cl2 (20 mL) at 0° C. The mixture was warmed to room temperature and stirred for about an hour and then extracted with ethyl acetate (50 mL). The organic layer was washed with H2O (3×50 mL) and brine (3×25 mL), and then 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. 1H-NMR (200.15 MHz, CDCl3): d 7.57–7.29 (m, 7H), 6.98 (dd, 2H, J=6.72, 1.88), 4.45 (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 brine (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-03df3146e5334da28ae2ccfc0460ab9b
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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