Carbon tetrabromide → HCID 22057750, compound

HRID 1828712Notes

Reaction equation

HRID 1828712 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH2:9]O)[CH:6]=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:37]>C(Cl)Cl>[Br:37][CH2:9][C:7]1[CH:6]=[CH:5][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:3]([CH2:1][CH3:2])[CH:8]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22057732HCID 22057732, compound

Product 1

HCID 22057750HCID 22057750, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of (2-ethyl-biphenyl-4-yl)-methanol (780 mg, 3.67 mmol) and PPh3 (1.44 g, 5.5 mmol) in DCM (15 mL) at 0° C. is added CBr4 (1.82 g, 5.5 mmol) in DCM (2 mL). The reaction is stirred at 0° C. for 1 h followed by concentration. The residue obtained is purified by silica gel chromatography (5% EtOAc in hexanes) to give 4-bromomethyl-2-ethyl-biphenyl as a colorless oil.

Workup

  1. concentrationfollowed by concentration
  2. customThe residue obtained
  3. customis purified by silica gel chromatography (5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5f2c0034743b4f15b6c39d70259ff01f
Source dataset
uspto-grants-2006_06
Patent number
US07060697B2

Reaction notes

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