Toluene → 3-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-benzoyl chloride

HRID 1665255Notes

Reaction equation

HRID 1665255 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20](O)=[O:21])=[CH:11][CH:10]=2)=[C:4]([O:26][CH3:27])[CH:3]=1.C1(C)C=CC=CC=1.O=S(Cl)[Cl:37]>CN(C=O)C>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([Cl:37])=[O:21])=[CH:11][CH:10]=2)=[C:4]([O:26][CH3:27])[CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 582711913-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-benzoic acid

Product 1

HCID 866535923-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-benzoyl chlorideYield 98.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-benzoic acid (16.44 g, 44.39 mmol), toluene (180 mL), SOCl2 (19.4 mL, 265.8 mmol), and anhydrous DMF (1 mL) was heated to reflux overnight, cooled to room temperature, and evaporated to dryness. The residue was co-evaporated twice with toluene followed by high vacuum at 70° C. for 4 h to give 3-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-benzoyl chloride as a solid (17 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-c5d4ce2955864862a50b9e51fd149ee7
Source dataset
uspto-grants-2011_10
Patent number
US08039495B2

Reaction notes

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