Hexane → Methyl 3-bromo-4-methylbenzoate

HRID 1839444Notes

Reaction equation

HRID 1839444 reaction equation
[CH3:1]CCCCC.[H-].[Na+].[Br:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:13]([OH:15])=[O:14]>CN(C=O)C.CCOC(C)=O>[Br:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:13]([O:15][CH3:1])=[O:14]

Participants

6

Reactant 3

HCID 8058HexaneHCID 24758Sodium hydrideHCID 821303-Bromo-4-methylbenzoic acid

Product 1

HCID 7015747Methyl 3-bromo-4-methylbenzoateYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of hexane washed 60% disp. NaH (2.28 g, 57 mmol) in DMF (250 mL), 0 C., was added 3-bromo-4-methylbenzoic acid (10.03 g, 46.6 mmol) After 30 min, the reaction was warmed to room temperature, diluted with EtOAc (1.25 L) and washed with H2O (5×250 mL). The organic layer was MgSO4 dried and concentrated. The residue was chromatographed (˜375 g silica, 10% EtOAc/CH2Cl2) to give the desired product as a solid (16.68 g, 63%); IR(CHCl3): 1260, 1294, 1437, 1721 cm−1; NMR(300 MHz, CDCl3): 2.46 (s, 3H); 3.92 (s, 3H); 7.31 (d, 1H, J=7.8 Hz); 7.88 (d, 1H, J=7.8 Hz); 8.21 (s, 1H); MS(FD): 228.0.

Workup

  1. washwashed 60%
  2. washwashed with H2O (5×250 mL)
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was chromatographed (˜375 g silica, 10% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-3ca452f274e14d73b62fb75da97099e4
Source dataset
uspto-grants-2004_01
Patent number
US06677369B2

Reaction notes

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