Acetic Acid Mixture with Hydrobromic Acid → HCID 21930359, compound

HRID 1243748Notes

Reaction equation

HRID 1243748 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12]C)=[CH:8][C:3]=1[CH2:4][N:5]([CH3:7])[CH3:6].[BrH:14].C(O)(=O)C>>[BrH:14].[CH3:7][N:5]([CH2:4][C:3]1[CH:8]=[C:9]([OH:12])[CH:10]=[CH:11][C:2]=1[F:1])[CH3:6]

Participants

3

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 219304071-(2-Fluoro-5-methoxyphenyl)-N,N-dimethylmethanamine

Product 1

HCID 21930359HCID 21930359, compoundYield 69%

Procedure

(2-Fluoro-5-methoxybenzyl)-dimethylamine (1.51 g, 8.24 mmol) was heated to reflux in 30% hydrogen bromide/acetic acid (10 mL) for 17 h. The cooled reaction mixture was triturated and decanted with successive portions of diethyl ether (4×), then triturated with diethyl ether overnight. The solid was collected by filtration, washed with ether and dried to give 3-dimethylaminomethyl-4-fluorophenol hydrobromide (1.43 g, 69%) as a tan solid.

Workup

  1. customThe cooled reaction mixture
  2. customwas triturated
  3. customdecanted with successive portions of diethyl ether (4×)
  4. customtriturated with diethyl ether overnight
  5. filtrationThe solid was collected by filtration
  6. washwashed with ether
  7. customdried

Sources & evidence

ORD record
ord-f12eab27b9f645319f1cdd3d4c4f4b24
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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