Water → 1-[Bromo(phenyl)methyl]naphthalene

HRID 41324Notes

Reaction equation

HRID 41324 reaction equation
[C:1]1([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:20].O>C(OCC)C>[Br:20][CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 226163Naphthalen-1-yl(phenyl)methanol

Product 1

HCID 582386271-[Bromo(phenyl)methyl]naphthaleneYield 138.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 32.3 g (138 mmol) of 7 in 150 mL of dry diethyl ether, 24.8 g (8.62 mL, 91.6 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 37.7 g (92%) of 8.

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-803a1df4ba5f4e028f869e71911b3ae9
Source dataset
uspto-grants-2013_09
Patent number
US08530593B2

Reaction notes

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