Benzyl Bromide → 4-(Benzyloxy)-3-fluorobenzaldehyde

HRID 82779

Reaction equation

HRID 82779 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[CH2:11]([O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[F:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 5872503-Fluoro-4-hydroxybenzaldehyde

Product 1

HCID 219768984-(Benzyloxy)-3-fluorobenzaldehydeYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-fluoro-4-hydroxybenzaldehyde (4.264 g, 30.0 mmol), benzyl bromide (5.986 g, 35.0 mmol, 4.16 mL) and K2CO3 (820 g, 59.0 mmol) in DMF (50 mL) was stirred for 48 hours at room temperature before EtOAc (100 mL) and water (50 mL) were added. The organic layer was separated, washed with water (2×50 mL), brine (30 mL) and dried (Na2SO4). Concentration in vacuo gave a white solid residue. Recrystallization from CH2Cl2/n-hexane afforded CAB06038 as colorless needles (5.59 g, 81%). Mp. 94-95° C.; 1H NMR (400 MHz, CDCl3) δ 524 (s, 2H), 7.12 (dd, J=8.2, 8.2 Hz, 1H), 734-7.48 (m, 5H), 7.59-7.66 (m, 2H), 9.85 (d, J=2.0 Hz, 1H); LRMS (ES+): m/z 231.1 (100%, [M+H]+).

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. washwashed with water (2×50 mL), brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationConcentration in vacuo
  6. customgave a white solid residue
  7. customRecrystallization from CH2Cl2/n-hexane

Sources & evidence

ORD record
ord-3841b984b0134e28bf554ba3eafab8b1
Source dataset
uspto-grants-2014_09
Patent number
US08846737B2

Linked notes

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