Phosphorus tribromide → 4-(1-Bromoethyl)-1,2-dichlorobenzene

HRID 1504490Notes

Reaction equation

HRID 1504490 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9](O)[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].P(Br)(Br)[Br:13]>CCCCCCC.CCOCC.N1C=CC=CC=1>[Br:13][CH:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH3:10]

Participants

6

Reactant 2

HCID 24614Phosphorus tribromideHCID 978993,4-Dichloro-alpha-methylbenzenemethanol

Product 1

HCID 431414504-(1-Bromoethyl)-1,2-dichlorobenzeneYield 170.4%

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 3283Diethyl EtherSolvent2×HCID 8900HeptaneSolvent

Procedure

To a solution of 1-(3,4-dichlorophenyl)ethanol (0.87 g, 4.55 mmol)in n-heptane (5.00 mL) and Et2O (0.500 mL) at 0° C. was added pyridine (1 drop) and phosphorous tribromide (0.214 mL, 2.277 mmol). The reaction mixture was warmed to RT and stirred for 2 h. The reaction was diluted with ether, washed with water (1×), saturated NaHCO3 (1×), and brine (1×). The organic layer was dried over magnesium sulfate, filtered, and concentrated to give 4-(1-bromoethyl)-1,2-dichlorobenzene (0.985 g, 3.88 mmol, 85% yield). m/z (ESI) 249.0 (M+H)+.

Workup

  1. washwashed with water (1×), saturated NaHCO3 (1×), and brine (1×)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d0bd477f6a3f46cea7d294c96ea373f7
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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