Isobutanol → 4-Bromo-2-(2-methylpropoxy)benzoic acid

HRID 2220407Notes

Reaction equation

HRID 2220407 reaction equation
[H-].[Na+].[CH3:3][CH:4]([CH3:7])[CH2:5][OH:6].[Br:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11](F)[CH:10]=1>CN(C)C=O>[Br:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([O:6][CH2:5][CH:4]([CH3:7])[CH3:3])[CH:10]=1

Participants

5

Reactant 3

HCID 6560IsobutanolHCID 24758Sodium hydrideHCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 248246454-Bromo-2-(2-methylpropoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (60% w/w, 20.5 g) in N,N-dimethylformamide (365 ml) was added 2-methyl-1-propanol (48.7 ml) dropwise below 30° C. over 2 hours under nitrogen atmosphere. To the mixture was added 4-bromo-2-fluorobenzoic acid (50.0 g) slowly below 35° C. To the reaction mixture was added N,N-dimethylformamide (600 ml) and the mixture was stirred at room temperature for 4 days. The reaction mixture was partitioned between water (2000 ml) and hexane (1000 ml). The water layer was separated and acidified with 37% hydrochloric acid. The precipitate was collected by filtration, washed with water and dried at 55° C. to give 4-bromo-2-isobutoxybenzoic acid (62.4 g) as a white solid.

Workup

  1. customThe reaction mixture was partitioned between water (2000 ml) and hexane (1000 ml)
  2. customThe water layer was separated
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried at 55° C.

Sources & evidence

ORD record
ord-d24519aaa6464469aff2a413ad942d50
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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