Boron trifluoride → 4,4-Dimethyl-6,7-dimethoxy-1-bromomethylisochroman

HRID 223233

Reaction equation

HRID 223233 reaction equation
[CH3:1][C:2]([CH3:15])([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1)[CH2:3][OH:4].[Br:16][CH2:17][CH:18]=O.B(F)(F)F>[N+](C)([O-])=O>[CH3:1][C:2]1([CH3:15])[C:5]2[C:10](=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=2)[CH:18]([CH2:17][Br:16])[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 105131Acetaldehyde, bromo-HCID 130157782-(3,4-Dimethoxyphenyl)-2-methylpropan-1-ol

Product 1

HCID 205230704,4-Dimethyl-6,7-dimethoxy-1-bromomethylisochroman

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

A 2,2-Dimethyl-2-(3,4-dimethoxyphenyl)ethanol (0.95 g, 0.0045 m) is stirred with 1.07 g (0.0054 m) of the ethyl acetal of bromoacetaldehyde and 0.19 g (0.0014 m) of BF3 .etherate in 25 ml of nitromethane for 15 hours. The mixture is partitioned between methylene chloride and aqueous sodium carbonate. The organic phase is dried over sodium sulfate and concentrated to yield 1.52 g of 4,4-dimethyl-6,7-dimethoxy-1-bromomethylisochroman. The nmr is consistent with the assigned structure.

Workup

  1. customThe mixture is partitioned between methylene chloride and aqueous sodium carbonate
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3e4b66a471a743eabefd0a20575541a1
Source dataset
uspto-grants-1982_10
Patent number
US04352805

Linked notes

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