Hydrochloric Acid → Benzyl 6-amino-3-bromo-2-methylbenzoate

HRID 1725900Notes

Reaction equation

HRID 1725900 reaction equation
[Br:1][C:2]1[C:3]([CH3:26])=[C:4]([C:15]([NH:18]C(OC(C)(C)C)=O)=[CH:16][CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].ClCCl.Cl>O1CCOCC1>[NH2:18][C:15]1[C:4]([C:5]([O:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:6])=[C:3]([CH3:26])[C:2]([Br:1])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 68864148Benzyl 3-bromo-6-[(tert-butoxycarbonyl)amino]-2-methylbenzoate

Product 1

HCID 68863679Benzyl 6-amino-3-bromo-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 126A, dichlormethane (20 mL), and 4N HCl in dioxane (30 mL) was stirred for 18 hours, concentrated, and triturated with a 1:1 mixture of hexanes and diethyl ether (150 mL) to provide the desired product. MS (ESI(+)) m/e 320, 322 (M+H)+; (ESI(−)) m/e 318, 320 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 7.40 (m, 5H), 7.31 (d, 1H), 6.56 (d, 1H), 5.33 (s, 2H), 4.92 (br s, 2H), 2.23 (s, 3H).

Workup

  1. concentrationconcentrated
  2. customtriturated with a 1:1 mixture of hexanes and diethyl ether (150 mL)

Sources & evidence

ORD record
ord-00ec7cb30b89404baff2a8541e4083f0
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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