Benzyl Alcohol → 1-(Benzyloxy)-3-bromo-5-chlorobenzene

HRID 656751Notes

Reaction equation

HRID 656751 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[C:4]([Cl:9])[CH:3]=1.[CH2:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[H-].[Na+].Cl>CN1C(=O)CCC1>[CH2:10]([O:17][C:6]1[CH:5]=[C:4]([Cl:9])[CH:3]=[C:2]([Br:1])[CH:7]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 27362231-Bromo-3-chloro-5-fluorobenzene

Product 1

HCID 532170081-(Benzyloxy)-3-bromo-5-chlorobenzene

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

To 1-bromo-3-chloro-5-fluorobenzene (25 g, 112 mmol) and benzyl alcohol (25 mL, 239 mmol) in NMP (200 mL) at room temperature was added sodium hydride (60% in mineral oil; 10.5 g, 263 mmol), and the reaction was heated to 120° C. for 10 hours. The mixture was acidified with 10% aqueous HCl and extracted with EtOAc to give the title compound.

Workup

  1. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-640618ca56354d879d804eaa3e4176c1
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

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