Oxalic Acid → HCID 58687480, compound

HRID 2052764Notes

Reaction equation

HRID 2052764 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[C:6]([F:9])[C:5]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:4][CH:3]=1.[Br:15][C:16]1[C:21]([C:22](O)=[O:23])=[C:20]([F:25])[C:19]([CH3:26])=[CH:18][CH:17]=1.C(O)(=O)C(O)=O>CN(C)C1C=CN=CC=1.ClCCl>[Br:15][C:16]1[C:21]([C:22]([O:8][C:7]2[C:2]([Br:1])=[CH:3][CH:4]=[C:5]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:6]=2[F:9])=[O:23])=[C:20]([F:25])[C:19]([CH3:26])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 58687474HCID 58687474, compoundHCID 586874916-Bromo-2-fluoro-3-methylbenzoic acid

Product 1

HCID 58687480HCID 58687480, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

43.2 g (0.165 mol) of 6-bromo-2-fluoro-3-pentylphenol, 40.5 g (0.173 mol) of 6-bromo-2-fluoro-3-methylbenzoic acid and 3.52 g (29 mmol) of 4-(dimethylamino)pyridine were initially introduced in 300 ml of dichloro-methane, and a solution of 35.7 g (0.172 mol) of N,N-dicyclohexyl-carbodiimide in 80 ml of dichloromethane was added. The batch was stirred overnight at room temperature, and 4.16 g (33 mmol) of oxalic acid were subsequently added. After 1 hour, the precipitated solid was filtered off, and the filtrate was evaporated under reduced pressure. The crude product was filtered through silica gel with n-heptane/1-chlorobutane (1:1), giving 72.7 g (91% of theory) of 6-bromo-2-fluoro-3-pentylphenyl 6-bromo-2-fluoro-3-methylbenzoate as a colourless oil.

Workup

  1. waitAfter 1 hour
  2. filtrationthe precipitated solid was filtered off
  3. customthe filtrate was evaporated under reduced pressure
  4. filtrationThe crude product was filtered through silica gel with n-heptane/1-chlorobutane (1:1)

Sources & evidence

ORD record
ord-521a524bffe74783b32cf2996a548cb7
Source dataset
uspto-grants-2008_02
Patent number
US07326447B2

Reaction notes

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