Hydrogen Bromide → 4-(4-hydroxyphenyl)benzaldehyde

HRID 1180329Notes

Reaction equation

HRID 1180329 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[F-].[K+].Br.Cl>CN(C=O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 260Hydrogen Bromide2×HCID 313Hydrochloric AcidHCID 522689Potassium FluorideHCID 42643333HCID 42643333, compound

Product 1

HCID 27592994-(4-hydroxyphenyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4′-{[tert-butyl(dimethyl)silyl]oxy}-1,1′-biphenyl-4-carbaldehyde (320 mg, 1.03 mmol), anhydrous KF (120 mg, 2.06 mmol) and 48% aqueous HBr (35 ul, 0.31 mmol) in 6 mL dry DMF was stirred at room temperature under N2 for 1 h. TLC indicated starting material present and therefore more 48% aqueous HBr (35 uL, 0.31 mmol) was added into the reaction and the mixture was continued to stir for 1.5 h. The mixture was then poured, with cooling, into 1 N aqueous HCl (30 mL). The aqueous mixture was extracted with EtOAc (3×). The combined extracts were washed with saturated NaCl solution, and dried over Na2SO4. The solvent was evaporated under reduced pressure and the product (100%) which was used directly in the next step. 1H NMR (DMSO-d6): δ 6.89 (2H, d, J=8.43 Hz), 7.63 (2H, d, J=8.46 Hz), 7.83 (2H, d, J=8.16 Hz), 7.94 (2H, d, J=8.02 Hz), 9.79 (1H, s), 10.01 (1H, s).

Workup

  1. stirringto stir for 1.5 h
  2. additionThe mixture was then poured
  3. extractionThe aqueous mixture was extracted with EtOAc (3×)
  4. washThe combined extracts were washed with saturated NaCl solution
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2f4f57df690c41b6bce1acbf771c126e
Source dataset
uspto-grants-2007_10
Patent number
US07279600B2

Reaction notes

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