Carbon tetrabromide → HCID 22105537, compound

HRID 1455960Notes

Reaction equation

HRID 1455960 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH:16](O)[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:39]>ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH:16]([Br:39])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22105598HCID 22105598, compound

Product 1

HCID 22105537HCID 22105537, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-(2-Benzyloxy-5-bromophenyl)-ethanol (3.69 g) was dissolved in dichloromethane (80 mL) and cooled to 0° C. under argon. Triphenyl phosphine 93.47 g) was added followed by carbon tetrabromide (7.36 g) and stirred for eighteen hours, allowing to warm to ambient temperature. After removal of solvent the residue was purified by MPLC (eluting 50% dichloromethane, 50% hexane, silica) to give 1-(2-benzyloxy-5-bromophenyl)ethyl bromide (2.9 g) which was used immediately without further purification.

Workup

  1. temperatureto warm to ambient temperature
  2. customAfter removal of solvent the residue
  3. customwas purified by MPLC (eluting 50% dichloromethane, 50% hexane, silica)

Sources & evidence

ORD record
ord-886822aae82644b9a51c8ddb3e9907d4
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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