Bromine → 5-bromo-3-tert-butyl-2-hydroxybenzaldehyde

HRID 1924442Notes

Reaction equation

HRID 1924442 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:5]([O:10]C)=[C:6]([CH:9]=1)[CH:7]=[O:8].C(C1C(O)=C(C=CC=1)C=O)(C)(C)C.BrBr>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 24408BromineHCID 36786753-tert-Butyl-2-hydroxybenzaldehydeHCID 11747664HCID 11747664, compound

Product 1

HCID 7970065-bromo-3-tert-butyl-2-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-bromo-3-tert-butyl-2-methoxybenzaldehyde (28)—To a solution of 3-tert-butyl-2-hydroxybenzaldehyde (CASRN 24623-65-2, 5.00 g) DCM (20 mL) at 0° C. was added dropwise a solution of Br2 (1.45 mL) in DCM (15 mL) over a period of 30 min. After the addition was complete the reaction was stirred for 1 h before the organic volatiles were removed under reduced pressure to afford 7.23 g of 5-bromo-3-tert-butyl-2-hydroxybenzaldehyde (27) as a light yellowish solid.

Workup

  1. additionAfter the addition
  2. customwere removed under reduced pressure

Sources & evidence

ORD record
ord-9ce13456df3d44ecb7654a34fe30b942
Source dataset
uspto-grants-2012_05
Patent number
US08178547B2

Reaction notes

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