Methanol → 3-(4-Fluoro-3-(methylsulfonyl)phenyl)-4-hydroxybenzaldehyde

HRID 68609Notes

Reaction equation

HRID 68609 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=2[O:16]C)[CH:11]=[O:12])=[CH:4][C:3]=1[S:18]([CH3:21])(=[O:20])=[O:19].B(Br)(Br)Br.CO>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=2[OH:16])[CH:11]=[O:12])=[CH:4][C:3]=1[S:18]([CH3:21])(=[O:19])=[O:20]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 866818393-(4-Fluoro-3-(methylsulfonyl)phenyl)-4-methoxybenzaldehyde

Product 1

HCID 866818403-(4-Fluoro-3-(methylsulfonyl)phenyl)-4-hydroxybenzaldehydeYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution (0° C.) of 3-(4-fluoro-3-(methylsulfonyl)phenyl)-4-methoxybenzaldehyde (27) (400 mg, 1.3 mmol, 1 eq.) in DCM (20 mL) was added BBr3 (0.4 mL). The reaction mixture was stirred room temperature for 3 h. After cooling to 0° C., methanol was added and the mixture was concentrated under vacuum. The residue was diluted with DCM and washed with water. The DCM was dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography (eluent: PE:EA=1:1) to give 340 mg (89%) of 3-(4-fluoro-3-(methylsulfonyl)phenyl)-4-hydroxybenzaldehyde (28).

Workup

  1. temperatureAfter cooling to 0° C.
  2. concentrationthe mixture was concentrated under vacuum
  3. additionThe residue was diluted with DCM
  4. washwashed with water
  5. dry with materialThe DCM was dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (eluent: PE:EA=1:1)

Sources & evidence

ORD record
ord-5206eb656afe4184b7398ed2152178f5
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

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