Water → HCID 59589404, compound

HRID 629984Notes

Reaction equation

HRID 629984 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8]O)=[CH:6][CH:5]=[CH:4][C:3]=1[OH:10].P(Br)(Br)[Br:12].O>C(Cl)(Cl)Cl>[Br:12][CH2:8][C:7]1[C:2]([Cl:1])=[C:3]([OH:10])[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 155506102-Chloro-3-(hydroxymethyl)phenol

Product 1

HCID 59589404HCID 59589404, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 2-chloro-3-(hydroxymethyl)phenol (400 mg, 2.5 mmol) in anhydrous chloroform (8 mL) was added dropwise a solution of phosphorus tribromide (240 μL, 2.5 mmol) in anhydrous chloroform (2 mL) at 0° C. The mixture was stirred for 2 hours at room temperature. Water was added and extracted 3 times with dichloromethane. The combined organic phase was washed with brine and dried over magnesium sulfate. After evaporation of the solvent, 3-(bromomethyl)-2-chlorophenol was obtained (373 mg, 67% yield) and used for next step without further purification; 1H NMR (400 MHz, DMSO-d6): δ 4.70 (s, 2H), 6.94-6.97 (m, 1H), 7.02-7.04 (m, 1H), 7.13 (t, J=7.8 Hz, 1H), 10.32 (bs, 1H).

Workup

  1. extractionextracted 3 times with dichloromethane
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-770fa73318d6444a9e831d7f5ee49f50
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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