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Dichloromethane → tert-Butyl 2-bromobenzoate

HRID 475667
Notes
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Reaction equation

HRID 475667 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.C(Cl)Cl.[Br:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([OH:24])=[O:23].[C:29](O)([CH3:32])([CH3:31])[CH3:30]>CN(C1C=CN=CC=1)C>[C:29]([O:23][C:22](=[O:24])[C:21]1[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=1[Br:19])([CH3:32])([CH3:31])[CH3:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6386tert-ButanolHCID 69402-Bromobenzoic acidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 3804415tert-Butyl 2-bromobenzoateYield 101.8%

Reagents, catalysts & solvents 1

HCID 14284
4-(Dimethylamino)pyridine
Catalyst

Procedure

To a solution of DCC (32.8 g, 159 mmol) in DCM (200 mL, 2 mol) was added 2-bromobenzoic acid (32.0 g, 159 mmol) followed by DMAP (1.8 g, 15 mmol) and t-butyl alcohol (15.2 mL, 159 mmol). The mixture was stirred at room temperature for 16 hours, then filtered. The organic was washed with saturated NaHCO3 (200 mL), saturated aqueous NaCl, dried over MgSO4, filtered and concentrated under reduced pressure to yield compound A as an oil (41.6 g).

Workup

  1. filtrationfiltered
  2. washThe organic was washed with saturated NaHCO3 (200 mL), saturated aqueous NaCl
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4ef90c9125f846e686c1ecbb1df99ab3
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637562B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes