Water → 1-[Bromo(phenyl)methyl]-2-methylbenzene

HRID 41322Notes

Reaction equation

HRID 41322 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)O.P(Br)(Br)[Br:17].O>C(OCC)C>[Br:17][CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 956592-Methylbenzhydrol

Product 1

HCID 128754701-[Bromo(phenyl)methyl]-2-methylbenzeneYield 133.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 28.1 g (140 mmol) of 5 in 150 mL of dry diethyl ether, 25.6 g (8.89 mL, 94.4 mmol) of PBr3 was added at −10° C. The resulting mixture was stirred for 12 hr at room temperature and then added to 450 mL of cold water. The organic layer was separated, and the aqueous layer was extracted with 2×150 mL of water. The combined organic extracts were washed with aqueous NaHCO3, dried over Na2SO4, and then evaporated to dryness. This procedure gave 33.0 g (89%) of the title product.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with 2×150 mL of water
  3. washThe combined organic extracts were washed with aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-915105dd21c746c1af4b64082204c4ae
Source dataset
uspto-grants-2013_09
Patent number
US08530593B2

Reaction notes

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