2-Bromo-4-methylphenol → HCID 21071776, compound

HRID 1372164Notes

Reaction equation

HRID 1372164 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[H-].[Na+].Br[CH2:13][CH:14]([O:17][CH3:18])[O:15][CH3:16]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:13][CH:14]([O:17][CH3:18])[O:15][CH3:16]

Participants

5

Reactant 3

HCID 231092-Bromo-4-methylphenolHCID 24758Sodium hydrideHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 21071776HCID 21071776, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 2 L round bottom flask was cooled to 0° C. a solution of 2-bromo-4-methylphenol (25 g, 133.66 mmol) in anhydrous DMF (940 ml). Then NaH (10.7 g 60% in mineral oil, 267.3 mmol) was slowly added in small portions and the reaction was warmed to room temperature (approx. 0.5 h) after which 2-bromo-1,1-dimethoxy ethane (31.6 ml, 267.4 mmol) was added. The reaction was warmed to room temperature for 3 h and then to 100° C. for 4 h. The reaction was cooled, pass through a silica plug, and concentrated. The brown mixture was diluted with EtOAc, passed through a silica plug again to remove brown solids and concentrated to 24.0 g (65%) amber colored oil: 1H NMR (300 MHz, DMSO-d6): δ 2.23 (3H, s), 3.37 (6H, s), 4.00 (2H, d, J=5.2 Hz), 4.68 (1H, t, J=5.2 Hz), 7.03 (1H, d, J=8.4 Hz), 7.12 (1H, dd, J=8.4 Hz, 1.7 Hz), 7.40 (1H, d, J=1.7 Hz).

Workup

  1. additionwas added
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. additionThe brown mixture was diluted with EtOAc
  5. customto remove brown solids
  6. concentrationconcentrated to 24.0 g (65%)

Sources & evidence

ORD record
ord-5ec57042800a4bb185ea9212b3594c28
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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