Phosphorus tribromide → HCID 22164149, compound

HRID 1087894Notes

Reaction equation

HRID 1087894 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11]O)[C:6]=1[O:13][CH2:14][CH2:15][F:16].P(Br)(Br)[Br:18]>C(OCC)C>[Br:18][CH2:11][C:7]1[C:6]([O:13][CH2:14][CH2:15][F:16])=[C:5]([O:4][CH2:3][CH2:2][F:1])[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 22164153HCID 22164153, compound

Product 1

HCID 22164149HCID 22164149, compoundYield 243.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a manner similar to that described by Noller et al. (Organic Synthesis, Vol. II. p 358-360), 2.0 grams (0.086 mole) of 1,2-di(2-fluoroethoxy)-3-hydroxymethylbenzene and 1.1 ml (0.0032 mole) of phosphorus tribromide were reacted in 90 ml of cold (0° C.) diethyl ether. The reaction mixture was partitioned between water and diethyl ether. The organic phase was washed with an aqueous, saturated sodium chloride solution. The washed organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 2.3 grams of 3-bromomethyl-1,2-di(2fluoroethoxy)benzene as a solid, mp 99°-100° C.

Workup

  1. customThe reaction mixture was partitioned between water and diethyl ether
  2. washThe organic phase was washed with an aqueous, saturated sodium chloride solution
  3. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1302c5fcd0cd4683ae4f4c7c8fff3743
Source dataset
uspto-grants-1990_10
Patent number
US04960884

Reaction notes

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