Water → 1,1'-(1-Bromoethane-1,2-diyl)dibenzene

HRID 41321

Reaction equation

HRID 41321 reaction equation
[C:1]1([CH:7](O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:17].O>C(OCC)C>[Br:17][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 941781,2-Diphenylethanol

Product 1

HCID 124997111,1'-(1-Bromoethane-1,2-diyl)dibenzeneYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 12.0 (60.5 mmol) of 1,2-diphenylethanol in 50 mL of dry diethyl ether, 11.0 g (3.80 mL, 40.0 mmol) of PBr3 was added with vigorous stirring at −10° C. The resulting mixture was stirred for 12 hr at room temperature and then added to 350 mL of cold water. The organic layer was separated, and the aqueous layer was extracted with 2×100 mL of water. The combined organic extracts were washed with aqueous NaHCO3, dried over Na2SO4, and evaporated to dryness. This procedure gave 13.2 g (84%) of the title product.

Workup

  1. stirringThe resulting mixture was stirred for 12 hr at room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with 2×100 mL of water
  4. washThe combined organic extracts were washed with aqueous NaHCO3
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-955a6e2a0d374c7495f12d087392dfcb
Source dataset
uspto-grants-2013_09
Patent number
US08530593B2

Linked notes

Loading…