Water → HCID 54157105, compound

HRID 439563Notes

Reaction equation

HRID 439563 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([OH:9])[C:3]=1[O:10][CH3:11].F[C:13]1([O:21][CH3:22])C(O)=CC(F)=CC1.B(Br)(Br)Br.[CH:27](N(C(C)C)CC)(C)C.[CH3:36][O:37]CCl.[OH2:40]>C(Cl)Cl>[F:1][C:2]1[C:3]([O:10][CH2:11][O:37][CH3:36])=[C:4]([O:9][CH2:13][O:21][CH3:22])[C:5]([F:8])=[CH:6][C:7]=1[CH:27]=[O:40]

Participants

8

Reactant 6

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 25134Boron tribromideHCID 81531DiisopropylethylamineHCID 589439Phenol, 3,6-difluoro-2-methoxy-HCID 67745008HCID 67745008, compound

Product 1

HCID 54157105HCID 54157105, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1, 4-Difluoro-2-methoxy-3-hydroxybenzene (1.60 g, 9.99 mmol) was converted into 2, 5-difluoro-2-methoxy-3-hydroxybenzene (610 mg, 33%) according to the method as described in L. Kirk et al., J. Org. Chem., 51, 4073 (1986). This compound (350 mg, 1.86 mmol) was allowed to react with 1M solution of boron tribromide in methylene chloride in the same manner as in Example 2. The crude product obtained above was dissolved in methylene chloride (2 ml), and diisopropylethylamine (0.4 ml, 2.3 mmol) and methoxymethyl chloride (0.45 ml, 6.0 mmol) were added to the solution, which was stirred at room temperature for 1 hour. The reaction mixture was mixed with water, extracted with ethyl acetate-hexane and the extract was concentrated in vacuo. The residue was chromatographed on a column of silica gel to give 2, 5-difluoro-3, 4-bis (methoxymethyloxy) benzaldehyde (200 mg, 41%).

Workup

  1. customThe crude product obtained
  2. extractionextracted with ethyl acetate-hexane
  3. concentrationthe extract was concentrated in vacuo
  4. customThe residue was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-388bda3eb5334bfeb6683f9ceba816df
Source dataset
uspto-grants-1996_05
Patent number
US05514711

Reaction notes

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