Hydrochloric Acid → 4-(Bromomethyl)benzaldehyde

HRID 1371016Notes

Reaction equation

HRID 1371016 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.C1(C)C=CC=CC=1.[Br:13][CH2:14][C:15]1C=CC(C#N)=[CH:17][CH:16]=1.CC(C[AlH]CC(C)C)C.Cl>CCOC(C)=O.CCCCCC.C1COCC1>[Br:13][CH2:14][C:15]1[CH:3]=[CH:2][C:1]([CH:5]=[O:4])=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 22635083Tetrahydrofuran toluene

Product 1

HCID 112064214-(Bromomethyl)benzaldehyde

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a THF-toluene (2.4 L-0.24 L) solution of α-bromo-p-tolunitrile (266.4 g, 1.36 mol) maintained at an internal temperature bellow 0° C. was added DIBAL in hexane (1.0 M) (1.49 L, 1.49 mol) over a period of 2 h. After a period of 1.5 h, the reaction mixture was transferred via canula to a 3N HCl solution (8 L) at 0° C. To the resulting suspension EtOAc (4 L) and THF (0.8 L) were added. After stirring, the organic phase was separated and evaporated to give a yellow solid. The solid was stirred in 20% EtOAc in hexane (1.3 L) for 3 hours. After filtration and drying the title compound was obtained. (210 g).

Workup

  1. customthe organic phase was separated
  2. customevaporated
  3. customto give a yellow solid
  4. filtrationAfter filtration
  5. dry with materialdrying the title compound
  6. customwas obtained

Sources & evidence

ORD record
ord-06d06c91adf0402692dceed32bceabaa
Source dataset
uspto-grants-2003_06
Patent number
US06583126B2

Reaction notes

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